Process for the preparation of pesticides

ABSTRACT

The invention relates to a process for the preparation of compounds of the formula                    
     or, if appropriate, a tautomer thereof, in each case in the free form or in salt form, in which A, X, Y, Z, R 2 , R 3 , R 4 , R 5 , R 7 , R 9  and n are as defined in claim 1 and the C═N double bond marked with E has the E configuration, which comprises 
     a1) reacting either a compound of the formula (II) mentioned above with a compound of the formula (III) mentioned above, in which X 1  is a leaving group, or 
     a2) a compound of the formula (IV) mentioned above, if appropriate in the presence of a base, with a compound of the formula (V) mentioned above, or 
     b1) reacting a compound of the formula (VI) mentioned above with a compound of the formula R 7 —A—X 2  (VII), in which X 2  is a leaving group, and either further reacting the compound thus obtainable, of the formula (IV), for example according to method a2), or 
     b2) reacting it with hydroxylamine or a salt thereof, if appropriate in the presence of a basic or acid catalyst, and further reacting the compound thus obtainable, of the formula (II), for example according to method a1), or 
     c) reacting a compound of the formula (VIII), mentioned above with a C 1 -C 6 alkyl nitrite and further reacting the compound thus obtainable, of the formula (VI), for example according to method b), the E isomers of the compounds of the formulae (II), (IV) and (VI), a process for their preparation and their use for the preparation of compounds of the formula (I).

This application is a divisional of U.S. Ser. No. 08/762,217, filed Dec.6, 1996, now U.S. Pat. No. 6,156,925.

The invention relates to a process for the preparation of compounds ofthe formula

and, where appropriate, their tautomers, in each case in the free formor salt form, in which either

X is CH or N, Y is OR₁ and Z is O, or

X is N, Y is NHR₈ and Z is O, S or S(═O);

R₁ is C₁-C₄alkyl;

R₂ is H, C₁-C₄alkyl, halogeno-C₁-C₄alkyl, C₃-C₆cycloalkyl orC₁-C₄alkoxymethyl;

R₃ and R₄ independently of one another are H, C₁-C₄alkyl, C₁-C₄alkoxy,OH, CN, NO₂, a (C₁-C₄alkyl)₃—Si group, where the alkyl groups can beidentical or different, halogen, (C₁-C₄alkyl)S(═O)_(m),(halogeno-C₁-C₄alkyl)S(═O)_(m), halogeno-C₁-C₄alkyl orhalogeno-C₁-C₄alkoxy;

R₅ is C₁-C₆alkyl, halogeno-C₁-C₆alkyl, C₁-C₆alkoxy,halogeno-C₁-C₆alkoxy, C₁-C₆-alkylthio, halogen-C₁-C₆alkylthio,C₁-C₆alkylsulfinyl, halogeno-C₁-C₆-alkylsulfinyl, C₁-C₆alkyl-sulfonyl,halogeno-C₁-C₆alkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkyl,halogeno-C₁-C₆alkoxy-C₁-C₆alkyl, C₁-C₆alkylthio-C₁-C₆alkyl,halogeno-C₁-C₆alkylthio-C₁-C₆alkyl, C₁-C₆alky sulfinyl-C₁-C₆alkyl,halogeno-C₁-C₆-alkylsulfinyl-C₁-C₆alkyl, C₁-C₆-alkylsulfonyl-C₁-C₆alkyl,halogeno-C₁-C₆-alkylsulfonyl-C₁-C₆alkyl, C₁-C₆-alkylcarbonyl,halogeno-C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl,halogeno-C₁-C₆-alkoxycarbonyl, C₁-C₆-alkyl-aminocarbonyl,C₁-C₄-alkoxyiminomethyl; di(C₁-C₆alkyl)-aminocarbonyl, where the alkylgroups can be identical or different; C₁-C₆-alkylaminothiocarbonyl;di(C₁-C₆alkyl)-aminothiocarbonyl, where the alkyl groups can beidentical or different; C₁-C₆-alkyl-amino, di(C₁-C₆alkyl)-amino, wherethe alkyl groups can be identical or different; halogen, NO₂, CN, SF₅,thioamido, thiocyanatomethyl; an unsubstituted or mono- totetrasubstituted C₁-C₄alkylenedioxy group, where the substituents areselected from the group consisting of C₁-C₄alkyl and halogen; or QR₆,where, if n is greater than 1, the radicals R₅ can be identical ordifferent;

R₆ is C₂-C₆alkenyl or C₂-C6 alkynyl which are unsubstituted orsubstituted by 1 to 3 halogen atoms; (C₁-C₄alkyl)₃Si, where the alkylgroups can be identical or different; CN; or an unsubstituted or mono-to pentasubstituted C₃-C₆cycloalkyl, aryl or heterocyclyl group, wherethe substituents are selected from the group consisting of halogen,C₁-C₆alkyl, halogeno-C₁-C₆alkyl, C₁-C₆alkoxy, halogeno-C₁-C₆alkoxy,phenoxy, naphthoxy and CN;

A either is a direct bond, C₁-C₁₀alkylene, —C(═O)—, —C(═S)— orhalogeno-C₁-C₁₀alkylene and R₇ is a radical R₁₀, or is C₁-C₁₀alkylene,—C(═O)—, —C(═S)— or halogeno-C₁-C₁₀alkylene and R₇ is OR₁₀, N(R₁₀)₂,where the radicals R₁₀ can be identical or different, or—S(═O)_(q)R_(10;)

R₈ is H or C₁-C₄alkyl;

R₉ is methyl, fluoromethyl or difluoromethyl;

R₁₀ is H; an unsubstituted or substituted C₁-C₆alkyl, C₂-C₆alkenyl orC₂-C₆alkynyl group, where the substituents are selected from the groupconsisting of halogen; (C₁-C₄alkyl)₃Si, where the alkyl groups can beidentical or different; C₃-C₆cyclo-alkyl, which is unsubstituted orsubstituted by halogen; C₁-C₆alkoxycarbonyl, which is unsubstituted orsubstituted by halogen; unsubstituted or substituted aryl, where thesubstituents are selected from the group consisting of halogen,halogeno-C₁-C₄alkyl and CN; a (C₁-C₄alkyl)₃Si group, where the alkylgroups can be identical or different; C₃-C₆cycloalkyl, which isunsubstituted or substituted by halogen; C₁-C₆alkoxycarbonyl which isunsubstituted or substituted by halogen; or an unsubstituted orsubstituted aryl or heterocyclyl group, where the substituents areselected from the group consisting of halogen and halogeno-C₁-C₄alkyl;

Q is a direct bond, C₁-C₈alkylene, C₂-C₆alkenylene, C₂-C₆alkynylene, O,O(C₁-C₆alkylene), (C₁-C₆alkylene)O, S(═O)p, S(═O)_(p)(C₁-C₆alkylene) or(C₁-C₆alkylene)S(═O)_(p);

m is 0, 1 or 2;

n is 0, 1, 2, 3, 4 or 5;

p is 0, 1 or 2; and

q is 0, 1 or 2,

and the C═N double bond marked with E has the E configuration,

which comprises

a1) reacting either a compound of the formula

 in which A, R₂, R₅, R₇ and n are as defined for formula I and the C═Ndouble bond marked with E has the E configuration, or a tautomerthereof, in each case in the free form or in salt form, if appropriatein the presence of a base, with a compound of the formula

 which is known or can be prepared by methods known per se and

in which X, Y, Z, R₃, R₄ and R₉ are as defined for formula I and X₁ is aleaving group, or a tautomer thereof, in each case in the free from orin salt form, or

a2) reacting a compound of the formula

 in which A, R₂, R₅, R₇ and n are as defined for formula I and the C═Ndouble bond marked with E has the E configuration, or a tautomerthereof, in each case in the free form or in the salt form, ifappropriate in the presence of a base, with a compound of the formula

 which is known or can be prepared by methods known per se and

in which X, Y, Z, R₃, R₄ and R₉ are as defined for formula I, or atautomer thereof, in each case in the free form or in salt form, or

b1) reacting a compound of the formula

 in which A, R₂, R₅ and n are as defined for formula I and the C═Ndouble bond marked with E has the E configuration, or a tautomerthereof, in each case in the free form or in salt form, if appropriatein the presence of a base, with a compound of the formula

R₇—A—X₂  (VII),

 which is known or can be prepared by methods known per se and

in which A and R₇ are as defined for formula I and X₂ is a leavinggroup, and either further reacting the compound thus obtainable, of theformula IV, for example according to method a1), or

b2) reacting it with hydroxylamine or a salt thereof, if appropriate inthe presence of a base or acid catalyst, and further reacting thecompound thus obtainable, of the formula II, for example according tomethod a1), or

c) reacting a compound of the formula

 which is known or can be prepared by methods known per se and

in which R₂, R₅ and n are as defined for formula I, or a tautomerthereof, in each case in the free form or in salt form, if appropriatein the presence of a base, with a C₁-C₆alkyl nitrite, and furtherreacting the compound thus obtainable, of the formula VI, for exampleaccording to method b),

the E isomers of the compounds of the formulae II, IV and VI, or atautomer thereof, in each case in the free form or in salt form, aprocess for their preparation and their use for the preparation ofcompounds of the formula I.

The compounds of the formula I are known pesticides. The processes knownto date for their preparation give mixtures of E and Z isomers inrespect of the C═N double bond marked with E in formula I of differentcomposition, depending on the process. Since the biological propertiesof the E isomers are in each case found to be superior to those of themixtures and of the Z isomers, there is a need to develop preparationprocesses for compounds of the formula I having the isomerically pure Econfiguration. This object is achieved by the preparation processaccording to the invention.

Unless defined differently, the general terms used above and below aredefined as follows.

Carbon-containing groups and compounds in each case contain 1 up to andincluding 8, preferably 1 up to and including 6, in particular 1 up toand including 4, especially 1 or 2, carbon atoms.

Alkyl—as a group per se and as a structural element of other groups andcompounds, such as of halogenoalkyl, alkoxy, alkylthio, alkylsulfinyl,alkylsulfonyl, alkylcarbonyl, alkoxycarbonyl, halogenoalkoxycarbonyl,alkylaminocarbonyl, alkoxyiminomethyl, alkylaminothiocarbonyl andalkylamino—is, in each case taking into due consideration the number,included from case to case, of carbon atoms contained in thecorresponding group or compound, either straight-chain, i.e. methyl,ethyl, propyl, butyl, pentyl or hexyl, or branched, for exampleisopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl orisohexyl.

Alkenyl—as a group per se and as a structural element of other groupsand compounds, such as of halogenoalkenyl—is, in each case under dueconsideration of the number, included from case to case, of carbon atomscontained in the corresponding group or compound, either straight-chain,for example vinyl, 1-methylvinyl, allyl, 1-butenyl or 2-hexenyl, orbranched, for example iso-propenyl.

Alkynyl—as a group per se and as a structural element of other groupsand compounds, such as of halogenoalkynyl—is, in each case under dueconsideration of the number, included from case to case, of carbon atomscontained in the corresponding group or compound, either straight-chain,for example propargyl, 2-butynyl or 5-hexynyl, or branched, for example2-ethynylpropyl or 2-propargylisopropyl.

C₃-C₆cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

Alkylene—as a group per se and as a structural element of other groupsand compounds, such as of O(alkylene), (alkylene)O, S(═O)_(p)(alkylene),(alkylene)S(═O)_(p) or alkylenedioxy—is, in each case under dueconsideration of the number, included from case to case, of carbon atomscontained in the corresponding group or compound, either straight-chain,for example —CH₂CH₂—, —CH₂CH₂CH₂—or —CH₂CH₂CH₂CH₂—, or branched, forexample —CH(CH₃)—, —CH(C₂H₅)—, —C(CH₃)₂—, —CH(CH₃)CH₂— or—CH(CH₃)CH(CH₃)—.

Alkenylene is, in each case under due consideration of the number, fromcase to case, of carbon atoms contained in the corresponding compound,either straight-chain, for example vin-1,2-ylene, all-1,3-ylene,but-1-en-1,4-ylene or hex-2-en-1,6-ylene, or branched, for example1-methylvin-1,2-ylene.

Alkynylene is, in each case under due consideration of the number, fromcase to case, of carbon atoms contained in the corresponding compound,either straight-chain, for example propargylene, 2-butynylene or5-hexynylene, or branched, for example 2-ethynylpropylene or2-propargylisopropylene.

Aryl is phenyl or naphthyl, in particular phenyl.

Heterocyclyl is a 5- to 7-membered aromatic or non-aromatic ring havingone to three heteroatoms, which are selected from the group consistingof N, O and S. 5- and 6-membered rings which contain a nitrogen atom asa heteroatom and, if appropriate, a further heteroatom, preferablynitrogen or sulfur, in particular nitrogen, are preferred.

Halogen—as a group per se and as a structural element of other groupsand compounds, such as of halogenoalkyl, halogenoalkenyl andhalogenoalkynyl—is fluorine, chlorine, bromine or iodine, especiallyfluorine, chlorine or bromine, in particular fluorine or chlorine, veryespecially fluorine.

Halogen-substituted carbon-containing groups and compounds, such ashalogenoalkyl, halogenoalkenyl or halogenoalkynyl, can be partlyhalogenated or perhalogenated, and in the case of polyhalogenation, thehalogen substituents can be identical or different. Examples ofhalogenoalkyl—as a group per se and as a structural element of othergroups and compounds, such as of halogenoalkenyl—are methyl which ismono- to trisubstituted by fluorine, chlorine and/or bromine, such asCHF₂ or CF₃; ethyl which is mono- to pentasubstituted by fluorine,chlorine and/or bromine, such as CH₂CF₃, CF₂CF₃, CF₂CCl₃, CF₂CHCl₂,CF₂CHF₂, CF₂CFCl₂, CF₂CHBr₂, CF₂CHClF, CF₂CHBrF or CClFCHClF; propyl orisopropyl which is mono- to heptasubstituted by fluorine, chlorineand/or bromine, such as CH₂CHBrCH₂Br, CF2CHFCF₃, CH₂CF₂CF₃ or CH(CF₃)₂;and butyl or one of its isomers which is mono- to nonasubstituted byfluorine, chlorine and/or bromine, such as CF(CF₃)-CHFCF₃orCH₂(CF₂)₂CF₃. Halogenoalkenyl is, for example, CH₂CH═CHCl, CH₂CH═CCl₂,CH₂CF═CF₂ or CH₂CH═CHCH₂Br. Halogenoalkynyl is, for example, CH₂C≡CF,CH₂C≡CCH₂Cl or CF₂CF₂C≡CCH₂F.

Some compounds I to VI and VII can be present as tautomers, as isfamiliar to the expert, in particular if AR₇ is H. Compounds I above andbelow are therefore also to be understood as meaning correspondingtautomers, even if the latter are not mentioned specifically in eachcase.

Compounds I to VI and VII which contain at least one basic centre, canform, for example, acid addition salts. These are formed, for example,with strong inorganic acids, such as mineral acids, for exampleperchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphoricacid, or a hydrogen halide acid, with strong inorganic carboxylic acids,such as C₁-C₄alkanecarboxylic acids which are unsubstituted orsubstituted, for example by halogen, for example acetic acid, such asdicarboxylic acids which are saturated or unsaturated, for exampleoxalic, malonic, succinic, maleic, fumaric or phthalic acid, such ashydroxycarboxylic acids, for example ascorbic, lactic, malic, tartaricor citric acid, or such as benzoic acid, or with organic sulfonic acids,such as C₁-C₄alkane- or arylsulfonic acids which are unsubstituted orsubstituted, for example by halogen, for example methane- orp-toluenesulfonic acid. Compounds I with at least one acid group canfurthermore form salts with bases. Suitable salts with bases are, forexample, metal salts such as alkali metal or alkaline earth metal salts,for example sodium, potassium or magnesium salts, or salts with ammoniaor an organic amine, such as morpholine, piperidine, pyrrolidine, amono-, di- or tri-lower alkylamine, for example ethyl-, diethyl-,triethyl- or dimethyl-propyl-amine, or a mono-, di- or trihydroxy-loweralkylamine, for example mono-, di- or triethanolamine. Furthermore,where appropriate, corresponding inner salts can be formed.Agrochemically advantageous salts are preferred in the context of theinvention; however, salts which have disadvantages for agrochemicaluses, for example salts which are toxic to bees or fish, which areemployed, for example, for isolation or purification of free compounds Ior agrochemically usable salts thereof, are also included. Compounds ofthe formulae I to VI and VII in the free form and in the form of theirsalts are also to be understood above and below as meaning thecorresponding salts or the free compounds I to VI and VII. The sameapplies to tautomers of compounds of the formulae I to VI and VII andsalts thereof. In general, the free form is in each case preferred.

The reactions described above and below are carried out in a mannerknown per se, for example in the absence or usually in the presence of asuitable solvent or diluent or a mixture thereof, the reaction beingcarried out, as required, with cooling, at room temperature or withheating, for example in a temperature range from about −80° C. up to theboiling point of the reaction medium, preferably from about 0° C. up toabout 150° C., and, if necessary, in a closed vessel, under pressure, inan inert gas atmosphere and/or under anhydrous conditions. Particularlyadvantageous reaction conditions can be seen from the examples.

The starting materials mentioned above and below, which are used for thepreparation of the compounds I, in each case in the free form or in saltform, are known or can be prepared by methods known per se, for examplein accordance with the following statements.

Variants a1/a2

Suitable leaving groups X₁ in compounds III are, for example, hydroxyl,C₁-C₈alkoxy, halogeno-C₁-C₈alkoxy, C₁-C₈alkanoyloxy, mercapto,C₁-C₈alkylthio, halogeno-C₁-C₈alkylthio, C₁-C₈alkanesulfonyloxy,halogeno-C₁-C₈alkanesulfonyloxy, benzenesulfonyloxy, toluenesulfonyloxyand halogen, preferably toluenesulfonyloxy, trifluoromethanesulfonyloxyand halogen, in particular halogen.

Suitable bases for facilitating the reaction are, for example, alkalimetal or alkaline earth metal hydroxides, hydrides, amides, alkanolates,acetates, carbonates, dialkylamides or alkylsilylamides, alkylamines,alkylenediamines, N-alkylated or non-alkylated, saturated or unsaturatedcycloalkylamines, basic heterocyclic compounds, ammonium hydroxides andcarbocyclic amines. Examples are sodium hydroxide, hydride, amide,methanolate, acetate and carbonate, potassium tert-butanolate,hydroxide, carbonate, and hydride, lithium diisopropylamide, potassiumbis(trimethylsilyl)amide, calcium hydride, triethylamine,diisopropyl-ethyl-amine, triethylenediamine, cyclohexylamine,N-cyclohexyl-N,N-dimethyl-amine, N,N-diethylaniline, pyridine,4-(N,N-dimethylamino)pyridine, quinuclidine, N-methylmorpholine,benzyl-trimethyl-ammonium hydroxide and1,5-diazabicyclo[5.4.0]undec-5-ene (DBU).

The reaction partners can be reacted with one another as such, i.e.without addition of a solvent or diluent, for example in the melt.However, the addition of an inert solvent or diluent or of a mixturethereof is usually advantageous. Examples of such solvents or diluentsare: aromatic, aliphatic and alicyclic hydrocarbons andhalogenohydrocarbons, such as benzene, toluene, xylene, mesitylene,tetralin, chlorobenzene, dichlorobenzene, bromobenzene, petroleum ether,hexane, cyclohexane, methylene chloride, chloroform, carbontetrachloride, dichloroethane, trichloroethene or tetrachloroethene;esters, such as ethyl acetate; ethers, such as diethyl ether, dipropylether, diisopropyl ether, dibutyl ether, tert-butyl methyl ether,ethylene glycol monomethyl ether, ethylene glycol monoethyl ether,ethylene glycol dimethyl ether, dimethoxydiethyl ether, tetrahydrofuranor dioxane; ketones, such as acetone, methyl ethyl ketone or methylisobutyl ketone; alcohols, such as methanol, ethanol, propanol,isopropanol, butanol, ethylene glycol or glycerol; amides, such asN,N-dimethylformamide, N,N-diethylformamide, N,N-dimethylacetamide,N-methylpyrrolidone or hexamethylphosphoric acid triamide; nitriles suchas acetonitrile or propionitrile; and sulfoxides, such as dimethylsulfoxide. If the reaction is carried out in the presence of a base,bases employed in excess, such as triethylamine, pyridine,N-methylmorpholine or N,N-diethylaniline, can also serve as the solventor diluent.

The reaction is advantageously carried out in a temperature range fromabout 0° C. up to about 180° C., preferably from about 10° C. up toabout 80° C., in many cases in the range between room temperature andthe reflux temperature of the reaction mixture.

The reaction is preferably carried out under normal pressure.

The reaction can be carried out without an inert gas atmosphere;preferably, however, it is carried out under an inert gas atmosphere,for example nitrogen or argon, in particular nitrogen.

The reaction time is not critical; a reaction time of about 0.1 to about24 hours, in particular about 0.5 to about 2 hours, is preferred.

The product is isolated by customary methods, for example by filtration,crystallization, distillation or chromatography or any suitablecombination of these processes.

In a preferred embodiment of variants a1/a2), a compound II is reactedwith a compound III at 0° C. to 80° C., preferably 10° C. to 30° C., inan inert solvent, preferably an amide, in particularN,N-dimethyiformamide in the presence of a metal hydride, preferablysodium hydride.

Particularly preferred conditions for the reaction are described inExamples H1d) and H3f).

The compounds of the formula III are known or can be preparedanalogously to known compounds. The compounds I are known. However,their preparation according to the prior art has a large number ofserious industrial, ecological, economic and other disadvantages.

Thus, in the preparation processes according to the prior art, as a ruleE/Z isomer mixtures with respect to the C═N double bond marked with E informula I are obtained. Since the biological properties of the E isomersare in each case found to be superior to those of the mixtures and ofthe Z isomers in each case, the processes according to the prior arthave the significant disadvantage that products are produced which areeither significantly less active as E/Z mixtures or from which the Zisomers must be removed in order to increase their biological activity,which means that many unnecessary handling operations must be carriedout for separation of isomers, which has the effect of being verytime-consuming, blocks valuable production lines for a long time and isassociated with high additional energy costs. The removal of the lessactive Z isomer also leads to additional enormous losses in yield, whichin turn not only is problematic and ecologically disadvantageous, butalso renders the process according to the prior art much more expensiveand consequently economically of no interest. The industrial,ecological, economic and other disadvantages of the processes accordingto the prior art are not limited to those described above, these latterbeing intended to serve only as a few examples of the large number ofdisadvantages of the processes according to the prior art. Thedisadvantages of the processes according to the prior art cause seriousproblems even when the processes are carried out on a laboratory scale.When the processes are carried out on a larger scale, thesedisadvantages intensify considerably. In the end, however, the aim is tocarry out a specific process on an industrial scale if this process isto be suitable for preparing products for agrochemical purposes.

According to the process of the present invention, the compounds I areprepared by reaction of the compound II with a compound III or byreaction of the compound IV with a compound V. These processes accordingto the invention have extremely surprising industrial, ecological,economic and other advantages compared with the processes from the priorart. Since the compounds II or, respectively, IV are present in thepreparation process according to the invention as pure E isomers inrespect of the C═N double bond marked with E, only the E isomer of thecompounds I is produced in the present process, which has the effect ofan enormous saving in time and at the same time a high saving in costand energy, since no valuable production lines are blocked for a longtime for separation of the isomers, and at the same time the amount ofbiologically more active E isomer produced by per unit time is muchhigher than in the processes according to the prior art. The resourcessuch as starting products and energy are consequently utilized to theoptimum in the present process, which not only very greatly simplifiesthe process and renders it ecologically advantageous, but consequentlyrenders it cheaper and therefore of greater economic interest. Thismeans that all the disadvantages of the processes according to the priorart which can be attributed to the formation of E/Z isomers are avoided.The industrial, ecological, economic and other advantages of the processaccording to the invention are not limited only to those describedabove, these latter being intended to serve only as a few examples ofthe large number of advantages inherent in this process. Due to all theabovementioned advantages of the present process, the serious problemswhich occur in the processes according to the prior art are avoided evenat the stage of a laboratory process. If the present process is used ona larger scale, these advantages prove to be even much more significant,which has the effect that these advantages first allow the process to beused on an industrial scale.

For this reason, all the industrial, ecological, economic and otherdisadvantages of the processes according to the prior art aresurprisingly advantageously overcome in the preparation of compounds Iby the present process.

Variant b)

The process according to variant b) is carried out by first reactingcompound VI with compound VII, if appropriate further reacting theresulting product IV, if appropriate after isolation, with hydroxylamineor a salt thereof, and further reacting the resulting products II or,respectively, IV, if appropriate after isolation, in accordance withvariants a1/a2), for example in the manner described above, to give thecompounds I.

Suitable leaving groups X₂ in the compounds VII are, for example, thosewhich are mentioned as examples for X₁ in variants a1/a2).

Suitable bases for facilitating the reaction are, for example, thosewhich are mentioned in variants a1/a2).

The reaction partners can be reacted with one another as such, i.e.without addition of a solvent or diluent, for example in the melt.However, the addition of an inert solvent or diluent or of a mixturethereof is usually advantageous. Examples of such solvents or diluentsare those mentioned in variants a1/a2).

The reaction is advantageously carried out in a temperature range fromabout 0° C. to about 180° C., preferably from about 10° C. to about 80°C., in many cases in the range between room temperature and the refluxtemperature of the reaction mixture.

The reaction is preferably carried out under normal pressure.

The reaction can be carried out without an inert gas atmosphere;preferably, however, it is carried out under an inert gas atmosphere,for example nitrogen or argon, in particular nitrogen.

The reaction time is not critical; a reaction time of about 0.1 to about24 hours, in particular about 0.5 to about 5 hours, is preferred.

The product is isolated by customary methods, for example filtration,crystallization, distillation or chromatography or any suitablecombination of these processes.

In a preferred embodiment of variant b), a compound VI is reacted with acompound VII at 0° C. to 80° C., preferably 10° C. to 60° C., in aninert solvent, preferably a nitrile, in particular acetonitrile, in thepresence of a metal carbonate, preferably potassium carbonate, and thecompound IV thus obtainable is then further reacted, preferably inaccordance with method a2).

Particularly preferred conditions for the reaction are described inExamples H 1 b) to 1 d) and H 3d) to 3f).

The compounds of the formula VII are known or can be preparedanalogously to known compounds.

The present process according to the invention of variant b), which inprinciple is an advantageous combination of an O-alkylation reactionwith process variants a1/a2) according to the invention, has all thegreat advantages compared with the prior art which have already beendiscussed above for the process according to the invention of variantsa1/a2). In particular, the process of variant b) ensures that the Econfiguration of the C═N double bond marked with E in compound VI isretained. Furthermore, however, the process according to the inventionof variant b) also has further industrial, ecological, economic andother advantages which are connected with the specific property that theintermediate product IV initially formed is not purified but is directlyfurther processed as the moist crude product, in the case ofintermediate isolation, or in situ in the reaction mixture, if it is notisolated. This missing purification step on the intermediate productmentioned is of advantage, for example, in as much as it is notnecessary to dry it, which not only saves energy and further resources,but also enormously increases the safety of the preparation process,since the possible danger of a dust explosion of the dry intermediateproduct is averted completely. The savings in resources are even greaterif the intermediate product is further reacted without purification,since, for example, no additional solvents are consumed for therecrystallization. The process of variant b) is of particular advantagecompared with the individual process steps of the alkylation reaction ofvariants a1/a2) carried out in that the total reaction time in theprocess of variant b) is much shorter, which consequently leads to amuch higher production of reaction product I per unit time and thereforeto a much more efficient utilization of the valuable production lines.Furthermore, the total yield of reaction product I is surprisingly goodwhen the process of variant b) is employed, and, compared with thecombined yields of the individual process steps of the alkylationreaction and variants a1/a2) carried out, is in the same percentagerange or even better. The industrial, ecological, economic and otheradvantages of the process according to the invention of variant b) arenot limited to those described above, these latter being intended toserve only as a few examples of the large number of advantages inherentin the process according to the invention of variant b).

By using process variant b) according to the invention for preparationof the compounds I, a large number of industrial, ecological, economicand other advantages can therefore surprisingly be utilized efficiently.

Variant c)

The process according to variant c) is carried out by first reactingcompound VII with an alkylnitrite and further reacting the resultingproduct VI, if appropriate after isolation, in accordance with variantb), for example in the manner described above, to give the compounds I.

Suitable bases for facilitating the reaction are, for example, thosewhich are mentioned in variants a1/a2).

The reaction partners can be reacted with one another as such, i.e.without addition of a solvent or diluent, for example in the melt.However, the addition of an inert solvent or diluent or of a mixturethereof is usually advantageous. Examples of such solvents or diluentsare those mentioned in variants a1/a2).

The reaction is advantageously carried out in a temperature range fromabout 0° C. to about 180° C., preferably from about 0° C. to about 60°C., in many cases in the range between room temperature and the refluxtemperature of the reaction mixture.

The reaction is preferably carried out under normal pressure.

The reaction can be carried out without an inert gas atmosphere;preferably, however, it is carried out under an inert gas atmosphere,for example nitrogen or argon, in particular nitrogen.

The reaction time is not critical; a reaction time of about 0.1 to about24 hours, in particular about 0.5 to about 3 hours, is preferred.

The product is isolated by customary methods, for example filtration,crystallization, distillation or chromatography or any suitablecombination of these processes.

In a preferred embodiment of variant c), a compound VII is reacted withan alkyl nitrite at 0° C. to 80° C., preferably 0° C. to 40° C., in aninert solvent, preferably an alcohol, in particular methanol, in thepresence of a metal alcoholate, preferably sodium methanolate, and thecompound VI thus obtainable is then further reacted, preferably inaccordance with method b).

Particularly preferred conditions for the reactions are described inExamples H 3d) to 3f).

The compounds of the formula VII are known or can be preparedanalogously to known compounds.

The present process according to the invention of variant c), which inprinciple is an advantageous combination of an oximation reaction withprocess variants a1/a2) and b) according to the invention, has all thegreat advantages compared with the prior art which have already beendiscussed above for the processes according to the invention of variantsa1/a2) and b). Furthermore, the present oximation process for thepreparation of the compounds VI surprisingly result exclusively in the Econfiguration of the C═N double bond marked with E in formula VI. It isthus ensured that the particular starting products II, IV or,respectively, VI in the subsequent processes according to the inventionfor the preparation of the compounds I, for example in process variantsa1/a2) and b), are pure E isomers.

A large number of industrial, ecological, economic and other advantagescan therefore surprisingly be utilized efficiently by using processvariants c) according to the invention for the preparation of thecompounds of the formula I.

The E isomers of the compounds of the formulae II, IV and VI andtautomers thereof, in each case in the free form or in salt form, arenovel and the present invention likewise relates to them.

The present invention furthermore relates to a process for thepreparation of the E isomers of a compound of the formula VI or of atautomer thereof, in each case in the free form or in salt form,according to the abovementioned process c),

a process for the preparation of the E isomers of a compound of theformula IV, or of a tautomer thereof, in each case in the free form orin salt form, according to the abovementioned process b1), and

a process for the preparation of the E isomers of a compound of theformula II, or of a tautomer thereof, in each case in the free form orin salt form, according to the abovementioned process b2).

The process conditions for the preparation of these intermediateproducts can be seen from the abovementioned processes a), b) and c).

PREPARATION EXAMPLES Example H1 Methyl2-[[[(1-methyl-2-phenyl-2-E-[(2-propynyl)oxyimino]-ethylidene)amino]oxy]methyl]α-(methoxymethylene)-phenylacetate(Compound 1.16)

H1a) 1-Phenyl-1,2-propanedione 1-E-oxime

69.7 g of a 30% solution of sodium methylate in methanol are addeddropwise to a solution of 40.2 g of 1-phenyl-2-propanone and 36.1 g ofisopentyl nitrite in 460 ml of methanol at 20-25°, while cooling. Thereaction mixture is then further stirred at room temperature for 1 hour.After the solution has been concentrated in vacuo, the residue isdissolved in 600 ml of water, the solution is acidified with 10%hydrochloric acid, the product which precipitates out is filtered offand dissolved in ethyl acetate and the organic phase is washed twicewith water, dried with sodium sulfate and evaporated in vacuo. Theresidue is stirred up in hexane and filtered. The title product is thusobtained with a melting of 168-70° C.

H1b) 1-Phenyl-1,2-propanedione 1-E-[(2-propynyl)oxime]

A mixture of 14 g of 1-phenyl-1,2-propanedione 1-E-oxime, 11.9 g of1-bromo-2-propyne, 13.8 g of potassium carbonate and 0.5 g of potassiumiodide in 170 ml of acetonitrile is stirred at 50° for 2 hours, thesolvent is then distilled off in vacuo and the residue is dissolvedagain in ethyl acetate. The organic phase is washed in each case twicewith water and saturated sodium chloride solution, dried with sodiumsulfate and evaporated in vacuo. After recrystallization of the residuefrom hexane, 1-phenyl-1,2-propanedione 1-E-[(2-propynyl)oxime] isobtained with a melting point of 54-56° C.

H1d) 1-Phenyl-1,2-propanedione 1-E-[(2-propynyl)oxime]-2-oxime

A mixture of 14.3 g of 1-phenyl-1,2-propanedione1-E-[(2-propynyl)oxime], 10.3 g of hydroxylamine hydrochloride and 11.7g of pyridine in 230 ml of ethanol is boiled under reflux for 1 hour andthen concentrated in vacuo, and 800 ml of water are added to theresidue. The product which has precipitated out is filtered off anddissolved in ethyl acetate and the solution is washed three times withwater, dried with sodium sulfate and evaporated in vacuo. The residue issuspended in hexane and filtered. The title product is thus obtainedwith a melting point of 163-165° C.

H1e) Methyl2-[[[(1-methyl-2-phenyl-2-E-[(2-propynyl)oxyimino]ethy-lidene)amino]oxy]-methyl]-α-(methoxymethylene)-phenylacetate

A solution of 5 g of 1-phenyl-1,2-propanedione1-E-[(2-propynyl)oxime]-2-oxime in 24 ml of N,N-dimethylformamide isadded dropwise to a suspension of 1.16 g of sodium hydride (about 55% inoil) in 45 ml of N,N-dimethylformamide at room temperature and themixture is further stirred for 10 minutes. 6.5 g of methyl2-(bromomethyl)-α-(methoxymethylene)-phenylacetate in 24 ml ofN,N-dimethylformamide are then added dropwise and the reaction mixtureis further stirred at room temperature for 1 hour. Thereafter, themixture is acidified with acetic acid and evaporated in vacuo. Theresidue is dissolved in ethyl acetate and the solution is washed threetimes with water and twice with saturated sodium chloride solution,dried with sodium sulfate and evaporated in vacuo. Afterrecrystallization of the residue from hexane/ethyl acetate, the titlecompound is obtained with a melting point of 82-84°.

Example H2 Methyl2-[[[(1-methyl-2-(4-fluorophenyl)-2-E-[(2-propynyl)oxyimino]ethylidene)amino]oxy]methyl]-α-(methoxymethylene)-phenylacetate (Compound 1.44)

The title compound with a melting point of 91-93° can be prepared in amanner analogous to that described in Example H1, starting from1-(4-fluorophenyl)-2-propanone.

Example H3 Methyl2-[[[(1-methyl-2-(4-(3-trifluoromethylphenylmethoxy)-phenyl)2-E-[(2-propynyl)oxyimino]ethylidene)amino]oxy]methyl]-α-(methoxymethylene)-phenylacetate(Compound 1.240)

H3a) 1-(4-Hydroxyphenyl)-2-propanone

A mixture of 82 g of 1-(4-methoxyphenyl)-2-propanone, 500 ml of aceticacid and 500 ml of aqueous hydrobromic acid is boiled under reflux for 2hours and then evaporated in vacuo. The oily residue is extracted fourtimes with 700 ml of hexane/ether (5:2) each time, the extract isevaporated and the residue is chromatographed over silica gel usinghexanelethyl acetate (3:1). 1-(4-Hydroxyphenyl)-2-propanone is thusobtained with a melting point of 40-41°.

H3b) 1-[4-(3-Trifluoromethylphenylmethoxy)-phenyl]-2-propanone

A mixture of 5.8 g of 1-(4-hydroxyphenyl)-2-propanone, 61.6 g ofpotassium carbonate, 72.3 g of1-(chloromethyl)-3-(trifluoromethyl)-benzene, and 1 g of potassiumiodide in 800 ml of acetone is boiled under reflux for 5 hours.Thereafter, the reaction mixture is filtered and the filtrate isevaporated in vacuo. The residue is then dissolved in diethyl ether andthe ethereal phase is washed three times with water, dried with sodiumsulfate and evaporated. The1-[4-(3-trifluoromethylphenylmethoxy)-phenyl]-2-propanone thusobtainable is employed in the next reaction stage without furtherpurification.

H3c) 1-[4-(3-Trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione1-E-oxime

45 g of a 30% solution of sodium methanolate in methanol are slowlyadded dropwise to a solution of 59.6 g of1-[4-(3-trifluoromethylphenylmethoxy)-phenyl]-2-propanone and 23.4 g ofisopentyl nitrite in 300 ml of methanol such that the temperature doesnot exceed 20-25°. The reaction mixture is then further stirred at roomtemperature for 1 hour and thereafter evaporated in vacuo. The residueis dissolved in 600 ml of water and the solution is acidified with 10%hydrochloric acid. The precipitate which separates out is filtered offand dissolved in ethyl acetate and the organic phase is washed twicewith water, dried with sodium sulfate and evaporated. After the crudeproduct has been suspended in hexane and filtered,1-[4-(3-trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione 1-E-oximeis obtained with a melting point of 134-136°.

H3d) 1-[4-(3-Trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione1-E-[(2-propynyl)oxime]

A mixture of 6 g of1-[4-(3-trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione1-E-oxime, 2.4 g of 1-bromo-2-propyne, 2.6 g of potassium carbonate and0.5 g of potassium iodide in 40 ml of acetonitrile is boiled underreflux for 1 hour and then evaporated in vacuo and the residue isdissolved in ethyl acetate. The organic phase is washed twice with waterand once with saturated sodium chloride solution, dried with sodiumsulfate and evaporated. The crude1-[4-(3-trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione1-E-[(2-propynyl)oxime] thus obtainable is further processed withoutfurther purification.

H3e) 1-[4-(3-Trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione1-E-[(2-propynyl)oxime]-2-oxime

A mixture of 5.9 g of1-[4-(3-trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione1-E-[(2-propynyl)oxime], 2.3 g of hydroxylamine hydrochloride and 2.6 gof pyridine in 60 ml of ethanol is boiled under reflux for 1 hour andthen concentrated in vacuo, and 200 ml of water are added to theresidue. The product which has precipitated out is filtered off anddissolved in ethyl acetate, and the solution is washed twice with waterand once with saturated sodium chloride solution, dried with sodiumsulfate and evaporated in vacuo. The residue is suspended in hexane andfiltered. 1-[4-(3-Trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione1-E-[(2-propynyl)oxime]-2-oxime is thus obtained with a melting point of114-115°.

H3f) Methyl2-[[[(1-methyl-2-(4-(3-trifluoromethylphenylmethoxy)-phenyl)-2-E-[(2-propynyl)oxyimino]ethylidene)amino]oxy]methyl]-α-(methoxymethylene)-phenylacetate

A solution of 5.5 g of1-[4-(3-trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione1-E-[(2-propynyl)oxime]-2-oxime in 25 ml of N,N-dimethylformamide isadded dropwise to a suspension of 0.7 g of sodium hydride (about 55% inoil) in 25 ml of N,N-dimethylformamide and the mixture is furtherstirred at room temperature for 10 minutes. 4 g of methyl2-(bromomethyl)-α-(methoxymethylene)-phenylacetate in 15 ml ofN,N-dimethylformamide are then added dropwise and the reaction mixtureis further stirred at room temperature for 1 hour. Thereafter, themixture is acidified with acetic acid and evaporated in vacuo at 50°.The residue is dissolved in ethyl acetate and the solution is washedtwice with water and once with saturated sodium chloride solution, driedwith sodium sulfate and evaporated in vacuo. After purification bychromatography (silica gel, ethyl acetate/hexane 1:3), the titlecompound is obtained as a resin.

Example H4 Methyl2-[[[(1-methyl-2-(4-(4-chlorophenoxy)-phenyl)-2-E-[(2-ethyl)oxyimino]ethylidene)amino]oxy]methyl]-α-(methoxymethylene)-phenylacetate(Compound 1.366)

H4a) 1-[4-(4-Chlorophenoxy)-phenyl]-1,2-propanedione 1-E-oxime

16.7 g of a 30% solution of sodium methylate in methanol are addeddropwise to a solution of 22.5 g of1-[4-(4-chlorophenoxy)-phenyl]-2-propanone and 10.3 g of isopentylnitrite in 120 ml of methanol at 20-25°, while cooling. The reactionmixture is then further stirred at room temperature for 1 hour. Afterthe solution has been concentrated in vacuo, the residue is dissolved in300 ml of water and the solution is acidified with 10% hydrochloricacid, the product which precipitates out is filtered off and dissolvedin ethyl acetate and the organic phase is washed twice with water, driedwith sodium sulfate and evaporated in vacuo. The residue is stirred upin hexane and filtered. The title product is thus obtained with amelting point of 154-155° C.

H4b) 1-[4-(4-Chlorophenoxy)-phenyl]-1,2-propanedione1-E-[(2-ethyl)oxime]

A mixture of 6 g of ) 1-[4-(4-Chlorophenoxy)-phenyl]-1,2-propanedione1-E-oxime, 3.3 g of ethyl bromide, 3.5 g of potassium carbonate and 0.5g of potassium iodide in 30 ml of acetonitrile is stirred at 500 for 2hours, the solvent is then distilled off in vacuo and the residue isdissolved again in ethyl acetate. The organic phase is washed in eachcase twice with water and saturated sodium chloride solution, dried withsodium sulfate and evaporated in vacuo. After recrystallization of theresidue from hexane, the title product is obtained with a melting pointof 77-78° C.

H4c) 1-[4-(4-Chlorophenoxy)-phenyl]-1,2-propanedione1-E-[(2-ethyl)oxime]-2-oxime

A mixture of 5.5 g of 1-[4-(4-chlorophenoxy)-phenyl]-1,2-propanedione1-E-[(2-ethyl)oxime], 2.4 g of hydroxylamine hydrochloride and 2.7 g ofpyridine in 50 ml of ethanol is boiled under reflux for 1 hour and thenconcentrated in vacuo, and 800 ml of water are added to the residue. Theproduct which has precipitated out is filtered off and dissolved inethyl acetate and the solution is washed three times with water, driedwith sodium sulfate and evaporated in vacuo. The residue is suspended inhexane and filtered. The title product is thus obtained in a pure formwith a melting point of 176-1770° C.

H4d) Methyl2-[[[(1-methyl-2-(4-(4-chlorophenoxy)-phenyl)-2-E-[(2-ethyl)oxyimino]ethylidene)amino]oxy]methyl]-α-(methoxymethylene)-phenylacetate.

A solution of 4.7 g of 1-[4-(4-chlorophenoxy)-phenyl]-1,2-propanedione1-E-[(2-propynyl)-oxime]-2-oxime in 25 ml of N,N-dimethylformamide isadded dropwise to a suspension of 0.65 g of sodium hydride (about 55% inoil) in 20 ml of N,N-dimethylformamide and the mixture is furtherstirred at room temperature for 10 minutes. 4 g of methyl2-(bromomethyl)-α-(methoxymethylene)-phenylacetate in 15 ml ofN,N-dimethylformamide are then added dropwise and the reaction mixtureis further stirred at room temperature for 1 hour. Thereafter, themixture is acidified with acetic acid and evaporated in vacuo at 50°.The residue is dissolved in ethyl acetate and the solution is washedtwice with water and once with saturated sodium chloride solution, driedwith sodium sulfate and evaporated in vacuo. After purification by flashchromatography (silica gel, ethyl acetate/hexane 1:3), the titlecompound is obtained with a melting point of 87-89° C.

Example H5 Methyl2-[[[(1-methyl-2-(4-(4-chlorophenoxy)-phenyl)-2-E-[(2-ethyl)oxy-imino]ethylidene)amino]oxy]methyl]-α-(methoxyimino)-phenylacetate(Compound 2.366)

The title compound with a melting point of 90 to 93° C. is obtained in amanner analogous to that described in Example H4 from1-[4-(4-chlorophenoxy)-phenyl]-1,2-propanedione1-E-[(2-propynyl)oxime]-2-oxime and methyl2-(bromomethyl)-α-(methoxyimino)-phenylacetate.

Example H62-[[[(1-Methyl-2-(4-(4-chlorophenoxy)-phenyl)-2-E-[(2-ethyl)oxy-imino]ethylidene)amino]oxy]methyl]-α-(methoxyimino)-phenylaceticacid methylamide (Compound 3.366)

13.3 g of methyl2-[[[(1-methyl-2-(4-(4-chlorophenoxy)-phenyl)-2-E-[(2-ethyl)oxyimino]ethyli-ene)amino]oxy]methyl]-α-(methoxyimino)-phenylacetateare left to stand together with 80 ml of dimethylformamide and 9.2 ml ofan 8 molar solution of methylamine in ethanol at room temperature fortwo days. The mixture is concentrated at 50° C., n-hexane is added andthe mixture is cooled to room temperature and filtered. The residue isdried under a high vacuum. The title compound is obtained with a meltingpoint of 126-129° C.

Example H7

The other compounds listed in Tables 1 to 3 can also be prepared in amanner analogous to that described in Examples H1 to H6. In the“physical data” column of the tables, the temperatures stated in eachcase designate the melting point of the compound in question. c.propylis cyclopropyl.

TABLE 1 Compounds of the general formula

in which X is CH and Y is oxygen and the combination of substituents R₂,(R₅)_(n) and A—R₇ for a compound in each case corresponds to a line inTable A. The compound numbers of the following table correspond to theparticular numbers in Table A. Compound No. Phys. Data (Melting point °C.) 1.14 75-77° 1.16 82-84° 1.22 111-113° 1.42 Resin 1.44 91-93° 1.50Resin 1.70 Resin 1.72 Resin 1.78 Resin 1.225 102-103° 1.226 81-83° 1.227Resin 1.233 Resin 1.234 73-75° 1.238 Resin 1.240 Resin 1.241 Resin 1.242Resin 1.244 Resin 1.245 Resin 1.294 Resin 1.296 112-114° 1.366 87-89°

TABLE 2 Compounds of the general formula I.1, in which X is nitrogen andY is oxygen and the combination of substituents R₂, (R₅)_(a) and A-R₇for a compound in each case corresponds to a line in Table A. CompoundNo. Melting point (° C.) 2.198 75-77 2.254 80-82 2.309 106-108 2.310102-104 2.366 90-93

TABLE 3 Compounds of the general formula I.1, in which X is nitrogen andY is NH and the combination of substituents R₂, (R₅)_(a) and A-R₇ for acompound in each case corresponds to a line in Table A. Compound No.Melting point (° C.) 3.198 75-77 3.254 112-114 3.309 89-91 3.310 88-903.366 126-129

TABLE A Com- pound No. R₂ (R₅)_(a) A—R₇ 1 CH₃ H CH₃ 2 CH₃ H C₂H₅ 3 CH₃ Hn-C₃H₇ 4 CH₃ H i-C₃H₇ 5 CH₃ H n-C₄H₉ 6 CH₃ H n-C₆H₁₃ 7 CH₃ H CH₂F 8 CH₃H CHF₂ 9 CH₃ H CH₂CF₃ 10 CH₃ H CH₂CH═CH₂ 11 CH₃ H CH₂CH═CHCH₃ 12 CH₃ HCH₂CH═C(CH₃)₂ 13 CH₃ H CH₂CH═CHCl 14 CH₃ H CH₂CH═CCl₂ 15 CH₃ HCH₂C(CH₃)═CH₂ 16 CH₃ H CH₂C≡CH 17 CH₃ H CH₂Si(CH₃)₃ 18 CH₃ HCH₂-c.propyl-2,2-Cl₂ 19 CH₃ H CH₂CN 20 CH₃ H CH₂COOC₂H₅ 21 CH₃ HCH(CH₃)COOC₂H₅ 22 CH₃ H CH₂C₆H₄-3-CF₃ 23 CH₃ H CH₂C₆H₄-4-F 24 CH₃ HCH₂C₆H₄-3-F 25 CH₃ H CH₂C₆H₄-2-F 26 CH₃ H C(═O)OC₂H₅ 27 CH₃ H C(═O)NHCH₃28 CH₃ H C(═O)C(═O)OC₂H₅ 29 CH₃ 4-F CH₃ 30 CH₃ 4-F C₂H₅ 31 CH₃ 4-Fn-C₃H₇ 32 CH₃ 4-F i-C₃H₇ 33 CH₃ 4-F n-C₄H₉ 34 CH₃ 4-F n-C₆H₁₃ 35 CH₃ 4-FCH₂F 36 CH₃ 4-F CHF₂ 37 CH₃ 4-F CH₂CF₃ 38 CH₃ 4-F CH₂CH═CH₂ 39 CH₃ 4-FCH₂CH═CHCH₃ 40 CH₃ 4-F CH₂CH═C(CH₃)₂ 41 CH₃ 4-F CH₂CH═CHCl 42 CH₃ 4-FCH₂CH═CCl₂ 43 CH₃ 4-F CH₂C(CH₃)═CH₂ 44 CH₃ 4-F CH₂C≡CH 45 CH₃ 4-FCH₂Si(CH₃)₃ 46 CH₃ 4-F CH₂-c.propyl-2,2-Cl₂ 47 CH₃ 4-F CH₂CN 48 CH₃ 4-FCH₂COOC₂H₅ 49 CH₃ 4-F CH(CH₃)COOC₂H₅ 50 CH₃ 4-F CH₂C₆H₄-3-CF₃ 51 CH₃ 4-FCH₂C₆H₄-4-F 52 CH₃ 4-F CH₂C₆H₄-3-F 53 CH₃ 4-F CH₂C₆H₄-2-F 54 CH₃ 4-FC(═O)OC₂H₅ 55 CH₃ 4-F C(═O)NHCH₃ 56 CH₃ 4-F C(═O)C(═O)OC₂H₅ 57 CH₃4-OCH₃ CH₃ 58 CH₃ 4-OCH₃ C₂H₅ 59 CH₃ 4-OCH₃ n-C₃H₇ 60 CH₃ 4-OCH₃ i-C₃H₇61 CH₃ 4-OCH₃ n-C₄H₉ 62 CH₃ 4-OCH₃ n-C₆H₁₃ 63 CH₃ 4-OCH₃ CH₂F 64 CH₃4-OCH₃ CHF₂ 65 CH₃ 4-OCH₃ CH₂CF₃ 66 CH₃ 4-OCH₃ CH₂CH═CH₂ 67 CH₃ 4-OCH₃CH₂CH═CHCH₃ 68 CH₃ 4-OCH₃ CH₂CH═C(CH₃)₂ 69 CH₃ 4-OCH₃ CH₂CH═CHCl 70 CH₃4-OCH₃ CH₂CH═CCl₂ 71 CH₃ 4-OCH₃ CH₂C(CH₃)═CH₂ 72 CH₃ 4-OCH₃ CH₂C≡CH 73CH₃ 4-OCH₃ CH₂Si(CH₃)₃ 74 CH₃ 4-OCH₃ CH₂-c.propyl-2,2-Cl₂ 75 CH₃ 4-OCH₃CH₂CN 76 CH₃ 4-OCH₃ CH₂COOC₂H₅ 77 CH₃ 4-OCH₃ CH(CH₃)COOC₂H₅ 78 CH₃4-OCH₃ CH₂C₆H₄-3-CF₃ 79 CH₃ 4-OCH₃ CH₂C₆H₄-4-F 80 CH₃ 4-OCH₃ CH₂C₆H₄-3-F81 CH₃ 4-OCH₃ CH₂C₆H₄-2-F 82 CH₃ 4-OCH₃ C(═O)OC₂H₅ 83 CH₃ 4-OCH₃C(═O)NHCH₃ 84 CH₃ 4-OCH₃ C(═O)C(═O)OC₂H₅ 85 CH₃ 4-OC₂H₅ CH₃ 86 CH₃4-OC₂H₅ C₂H₅ 87 CH₃ 4-OC₂H₅ n-C₃H₇ 88 CH₃ 4-OC₂H₅ i-C₃H₇ 89 CH₃ 4-OC₂H₅n-C₄H₉ 90 CH₃ 4-OC₂H₅ n-C₆H₁₃ 91 CH₃ 4-OC₂H₅ CH₂F 92 CH₃ 4-OC₂H₅ CHF₂ 93CH₃ 4-OC₂H₅ CH₂CF₃ 94 CH₃ 4-OC₂H₅ CH₂CH═CH₂ 95 CH₃ 4-OC₂H₅ CH₂CH═CHCH₃96 CH₃ 4-OC₂H₅ CH₂CH═C(CH₃)₂ 97 CH₃ 4-OC₂H₅ CH₂CH═CHCl 98 CH₃ 4-OC₂H₅CH₂CH═CCl₂ 99 CH₃ 4-OC₂H₅ CH₂C(CH₃)═CH₂ 100 CH₃ 4-OC₂H₅ CH₂C≡CH 101 CH₃4-OC₂H₅ CH₂Si(CH₃)₃ 102 CH₃ 4-OC₂H₅ CH₂-c.propyl-2,2-Cl₂ 103 CH₃ 4-OC₂H₅CH₂CN 104 CH₃ 4-OC₂H₅ CH₂COOC₂H₅ 105 CH₃ 4-OC₂H₅ CH(CH₃)COOC₂H₅ 106 CH₃4-OC₂H₅ CH₂C₆H₄-3-CF₃ 107 CH₃ 4-OC₂H₅ CH₂C₆H₄-4-F 108 CH₃ 4-OC₂H₅CH₂C₆H₄-3-F 109 CH₃ 4-OC₂H₅ CH₂C₆H₄-2-F 110 CH₃ 4-OC₂H₅ C(═O)OC₂H₅ 111CH₃ 4-OC₂H₅ C(═O)NHCH₃ 112 CH₃ 4-OC₂H₅ C(═O)C(═O)OC₂H₅ 113 CH₃4-O-n-C₃H₇ CH₃ 114 CH₃ 4-O-n-C₃H₇ C₂H₅ 115 CH₃ 4-O-n-C₃H₇ n-C₃H₇ 116 CH₃4-O-n-C₃H₇ i-C₃H₇ 117 CH₃ 4-O-n-C₃H₇ n-C₄H₉ 118 CH₃ 4-O-n-C₃H₇ n-C₆H₁₃119 CH₃ 4-O-n-C₃H₇ CH₂F 120 CH₃ 4-O-n-C₃H₇ CHF₂ 121 CH₃ 4-O-n-C₃H₇CH₂CF₃ 122 CH₃ 4-O-n-C₃H₇ CH₂CH-CH₂ 123 CH₃ 4-O-n-C₃H₇ CH₂CH═CHCH₃ 124CH₃ 4-O-n-C₃H₇ CH₂CH═C(CH₃)₂ 125 CH₃ 4-O-n-C₃H₇ CH₂CH═CHCl 126 CH₃4-O-n-C₃H₇ CH₂CH═CCl₂ 127 CH₃ 4-O-n-C₃H₇ CH₂C(CH₃)═CH₂ 128 CH₃4-O-n-C₃H₇ CH₂C≡CH 129 CH₃ 4-O-n-C₃H₇ CH₂Si(CH₃)₃ 130 CH₃ 4-O-n-C₃H₇CH₂-c.propyl-2,2-Cl₂ 131 CH₃ 4-O-n-C₃H₇ CH₂CN 132 CH₃ 4-O-n-C₃H₇CH₂COOC₂H₅ 133 CH₃ 4-O-n-C₃H₇ CH(CH₃)COOC₂H₅ 134 CH₃ 4-O-n-C₃H₇CH₂C₆H₄-3-CF₃ 135 CH₃ 4-O-n-C₃H₇ CH₂C₆H₄-4-F 136 CH₃ 4-O-n-C₃H₇CH₂C₆H₄-3-F 137 CH₃ 4-O-n-C₃H₇ CH₂C₆H₄-2-F 138 CH₃ 4-O-n-C₃H₇ C(═O)OC₂H₅139 CH₃ 4-O-n-C₃H₇ C(═O)NHCH₃ 140 CH₃ 4-O-n-C₃H₇ C(═O)C(═O)OC₂H₅ 141 CH₃2-CH₃ CH₃ 142 CH₃ 2-CH₃ C₂H₅ 143 CH₃ 2-CH₃ n-C₃H₇ 144 CH₃ 2-CH₃ i-C₃H₇145 CH₃ 2-CH₃ n-C₄H₉ 146 CH₃ 2-CH₃ n-C₆H₁₃ 147 CH₃ 2-CH₃ CH₂F 148 CH₃2-CH₃ CHF₂ 149 CH₃ 2-CH₃ CH₂CF₃ 150 CH₃ 2-CH₃ CH₂CH═CH₂ 151 CH₃ 2-CH₃CH₂CH═CHCH₃ 152 CH₃ 2-CH₃ CH₂CH═C(CH₃)₂ 153 CH₃ 2-CH₃ CH₂CH═CHCl 154 CH₃2-CH₃ CH₂CH═CCl₂ 155 CH₃ 2-CH₃ CH₂C(CH₃)═CH₂ 156 CH₃ 2-CH₃ CH₂C≡CH 157CH₃ 2-CH₃ CH₂Si(CH₃)₃ 158 CH₃ 2-CH₃ CH₂-c.propyl-2,2-Cl₂ 159 CH₃ 2-CH₃CH₂CN 160 CH₃ 2-CH₃ CH₂COOC₂H₅ 161 CH₃ 2-CH₃ CH(CH₃)COOC₂H₅ 162 CH₃2-CH₃ CH₂C₆H₄-3-CF₃ 163 CH₃ 2-CH₃ CH₂C₆H₄-4-F 164 CH₃ 2-CH₃ CH₂C₆H₄-3-F165 CH₃ 2-CH₃ CH₂C₆H₄-2-F 166 CH₃ 2-CH₃ C(═O)OC₂H₅ 167 CH₃ 2-CH₃C(═O)NHCH₃ 168 CH₃ 2-CH₃ C(═O)C(═O)OC₂H₅ 169 CH₃ 4-OCH₂Si(CH₃)₃ CH₃ 170CH₃ 4-OCH₂Si(CH₃)₃ C₂H₅ 171 CH₃ 4-OCH₂Si(CH₃)₃ n-C₃H₇ 172 CH₃4-OCH₂Si(CH₃)₃ i-C₃H₇ 173 CH₃ 4-OCH₂Si(CH₃)₃ n-C₄H₉ 174 CH₃4-OCH₂Si(CH₃)₃ n-C₆H₁₃ 175 CH₃ 4-OCH₂Si(CH₃)₃ CH₂F 176 CH₃4-OCH₂Si(CH₃)₃ CHF₂ 177 CH₃ 4-OCH₂Si(CH₃)₃ CH₂CF₃ 178 CH₃ 4-OCH₂Si(CH₃)₃CH₂CH═CH₂ 179 CH₃ 4-OCH₂Si(CH₃)₃ CH₂CH═CHCH₃ 180 CH₃ 4-OCH₂Si(CH₃)₃CH₂CH═C(CH₃)₂ 181 CH₃ 4-OCH₂Si(CH₃)₃ CH₂CH═CHCl 182 CH₃ 4-OCH₂Si(CH₃)₃CH₂CH═CCl₂ 183 CH₃ 4-OCH₂Si(CH₃)₃ CH₂C(CH₃)═CH₂ 184 CH₃ 4-OCH₂Si(CH₃)₃CH₂C≡CH 185 CH₃ 4-OCH₂Si(CH₃)₃ CH₂Si(CH₃)₃ 186 CH₃ 4-OCH₂Si(CH₃)₃CH₂-c.propyl-2,2-Cl₂ 187 CH₃ 4-OCH₂Si(CH₃)₃ CH₂CN 188 CH₃ 4-OCH₂Si(CH₃)₃CH₂COOC₂H₅ 189 CH₃ 4-OCH₂Si(CH₃)₃ CH(CH₃)COOC₂H₅ 190 CH₃ 4-OCH₂Si(CH₃)₃CH₂C₆H₄-3-CF₃ 191 CH₃ 4-OCH₂Si(CH₃)₃ CH₂C₆H₄-4-F 192 CH₃ 4-OCH₂Si(CH₃)₃CH₂C₆H₄-3-F 193 CH₃ 4-OCH₂Si(CH₃)₃ CH₂C₆H₄-2-F 194 CH₃ 4-OCH₂Si(CH₃)₃C(═O)OC₂H₅ 195 CH₃ 4-OCH₂Si(CH₃)₃ C(═O)NHCH₃ 196 CH₃ 4-OCH₂Si(CH₃)₃C(═O)C(═O)OC₂H₅ 197 CH₃ 4-OCH₂C₆H₄-4-CF₃ CH₃ 198 CH₃ 4-OCH₂C₆H₄-4-CF₃C₂H₅ 199 CH₃ 4-OCH₂C₆H₄-4-CF₃ n-C₃H₇ 200 CH₃ 4-OCH₂C₆H₄-4-CF₃ i-C₃H₇ 201CH₃ 4-OCH₂C₆H₄-4-CF₃ n-C₄H₉ 202 CH₃ 4-OCH₂C₆H₄-4-CF₃ n-C₆H₁₃ 203 CH₃4-OCH₂C₆H₄-4-CF₃ CH₂F 204 CH₃ 4-OCH₂C₆H₄-4-CF₃ CHF₂ 205 CH₃4-OCH₂C₆H₄-4-CF₃ CH₂CF₃ 206 CH₃ 4-OCH₂C₆H₄-4-CF₃ CH₂CH═CH₂ 207 CH₃4-OCH₂C₆H₄-4-CF₃ CH₂CH═CHCH₃ 208 CH₃ 4-OCH₂C₆H₄-4-CF₃ CH₂CH═C(CH₃)₂ 209CH₃ 4-OCH₂C₆H₄-4-CF₃ CH₂CH═CHCl 210 CH₃ 4-OCH₂C₆H₄-4-CF₃ CH₂CH═CCl₂ 211CH₃ 4-OCH₂C₆H₄-4-CF₃ CH₂C(CH₃)═CH₂ 212 CH₃ 4-OCH₂C₆H₄-4-CF₃ CH₂C≡CH 213CH₃ 4-OCH₂C₆H₄-4-CF₃ CH₂Si(CH₃)₃ 214 CH₃ 4-OCH₂C₆H₄-4-CF₃CH₂-c.propyl-2,2-Cl₂ 215 CH₃ 4-OCH₂C₆H₄-4-CF₃ CH₂CN 216 CH₃4-OCH₂C₆H₄-A-CF₃ CH₂COOC₂H₅ 217 CH₃ 4-OCH₂C₆H₄-4-CF₃ CH(CH₃)COOC₂H₅ 218CH₃ 4-OCH₂C₆H₄-4-CF₃ CH₂C₆H₄-3-CF₃ 219 CH₃ 4-OCH₂C₆H₄-4-CF₃ CH₂C₆H₄-4-F220 CH₃ 4-OCH₂C₆H₄-4-CF₃ CH₂C₆H₄-3-F 221 CH₃ 4-OCH₂C₆H₄-4-CF₃CH₂C₆H₄-2-F 222 CH₃ 4-OCH₂C₆H₄-4-CF₃ C(═O)OC₂H₅ 223 CH₃ 4-OCH₂C₆H₄-4-CF₃C(═O)NHCH₃ 224 CH₃ 4-OCH₂C₆H₄-4-CF₃ C(═O)C(═O)OC₂H₅ 225 CH₃4-OCH₂C₆H₄-3-CF₃ CH₃ 226 CH₃ 4-OCH₂C₆H₄-3-CF₃ C₂H₅ 227 CH₃4-OCH₂C₆H₄-3-CF₃ n-C₃H₇ 228 CH₃ 4-OCH₂C₆H₄-3-CF₃ i-C₃H₇ 229 CH₃4-OCH₂C₆H₄-3-CF₃ n-C₄H₉ 230 CH₃ 4-OCH₂C₆H₄-3-CF₃ n-C₆H₁₃ 231 CH₃4-OCH₂C₆H₄-3-CF₃ CH₂F 232 CH₃ 4-OCH₂C₆H₄-3-CF₃ CHF₂ 233 CH₃4-OCH₂C₆H₄-3-CF₃ CH₂CF₃ 234 CH₃ 4-OCH₂C₆H₄-3-CF₃ CH₂CH═CH₂ 235 CH₃4-OCH₂C₆H₄-3-CF₃ CH₂CH═CHCH₃ 236 CH₃ 4-OCH₂C₆H₄-3-CF₃ CH₂CH═C(CH₃)₂ 237CH₃ 4-OCH₂C₆H₄-3-CF₃ CH₂CH═CHCl 238 CH₃ 4-OCH₂C₆H₄-3-CF₃ CH₂CH═CCl₂ 239CH₃ 4-OCH₂C₆H₄-3-CF₃ CH₂C(CH₃)═CH₂ 240 CH₃ 4-OCH₂C₆H₄-3-CF₃ CH₂C≡CH 241CH₃ 4-OCH₂C₆H₄-3-CF₃ CH₂Si(CH₃)₃ 242 CH₃ 4-OCH₂C₆H₄-3-CF₃CH₂-c.propyl-2,2-Cl₂ 243 CH₃ 4-OCH₂C₆H₄-3-CF₃ CH₂CN 244 CH₃4-OCH₂C₆H₄-3-CF₃ CH₂COOC₂H₅ 245 CH₃ 4-OCH₂C₆H₄-3-CF₃ CH(CH₃)COOC₂H₅ 246CH₃ 4-OCH₂C₆H₄-3-CF₃ CH₂C₆H₄-3-CF₃ 247 CH₃ 4-OCH₂C₆H₄-3-CF₃ CH₂C₆H₄-4-F248 CH₃ 4-OCH₂C₆H₄-3-CF₃ CH₂C₆H₄-3-F 249 CH₃ 4-OCH₂C₆H₄-3-CF₃CH₂C₆H₄-2-F 250 CH₃ 4-OCH₂C₆H₄-3-CF₃ C(═O)OC₂H₅ 251 CH₃ 4-OCH₂C₆H₄-3-CF₃C(═O)NHCH₃ 252 CH₃ 4-OCH₂C₆H₄-3-CF₃ C(═O)C(═O)OC₂H₅ 253 CH₃4-OCH₂C₆H₄-2-CF₃ CH₃ 254 CH₃ 4-OCH₂C₆H₄-2-CF₃ C₂H₅ 255 CH₃4-OCH₂C₆H₄-2-CF₃ n-C₃H₇ 256 CH₃ 4-OCH₂C₆H₄-2-CF₃ i-C₃H₇ 257 CH₃4-OCH₂C₆H₄-2-CF₃ n-C₄H₉ 258 CH₃ 4-OCH₂C₆H₄-2-CF₃ n-C₆H₁₃ 259 CH₃4-OCH₂C₆H₄-2-CF₃ CH₂F 260 CH₃ 4-OCH₂C₆H₄-2-CF₃ CHF₂ 261 CH₃4-OCH₂C₆H₄-2-CF₃ CH₂CF₃ 262 CH₃ 4-OCH₂C₆H₄-2-CF₃ CH₂CH═CH₂ 263 CH₃4-OCH₂C₆H₄-2-CF₃ CH₂CH═CHCH₃ 264 CH₃ 4-OCH₂C₆H₄-2-CF₃ CH₂CH═C(CH₃)₂ 265CH₃ 4-OCH₂C₆H₄-2-CF₃ CH₂CH═CHCl 266 CH₃ 4-OCH₂C₆H₄-2-CF₃ CH₂CH═CCl₂ 267CH₃ 4-OCH₂C₆H₄-2-CF₃ CH₂C(CH₃)═CH₂ 268 CH₃ 4-OCH₂C₆H₄-2-CF₃ CH₂C≡CH 269CH₃ 4-OCH₂C₆H₄-2-CF₃ CH₂Si(CH₃)₃ 270 CH₃ 4-OCH₂C₆H₄-2-CF₃CH₂-c.propyl-2,2-Cl₂ 271 CH₃ 4-OCH₂C₆H₄-2-CF₃ CH₂CN 272 CH₃4-OCH₂C₆H₄-2-CF₃ CH₂COOC₂H₅ 273 CH₃ 4-OCH₂C₆H₄-2-CF₃ CH(CH₃)COOC₂H₅ 274CH₃ 4-OCH₂C₆H₄-2-CF₃ CH₂C₆H₄-3-CF₃ 275 CH₃ 4-OCH₂C₆H₄-2-CF₃ CH₂C₆H₄-4-F276 CH₃ 4-OCH₂C₆H₄-2-CF₃ CH₂C₆H₄-3-F 277 CH₃ 4-OCH₂C₆H₄-2-CF₃CH₂C₆H₄-2-F 278 CH₃ 4-OCH₂C₆H₄-2-CF₃ C(═O)OC₂H₅ 279 CH₃ 4-OCH₂C₆H₄-2-CF₃C(═O)NHCH₃ 280 CH₃ 4-OCH₂C₆H₄-2-CF₃ C(═O)C(═O)OC₂H₅ 281 CH₃4-OCH₂C₆H₄-4-F CH₃ 282 CH₃ 4-OCH₂C₆H₄-4-F C₂H₅ 283 CH₃ 4-OCH₂C₆H₄-4-Fn-C₃H₇ 284 CH₃ 4-OCH₂C₆H₄-4-F i-C₃H₇ 285 CH₃ 4-OCH₂C₆H₄-4-F n-C₄H₉ 286CH₃ 4-OCH₂C₆H₄-4-F n-C₆H₁₃ 287 CH₃ 4-OCH₂C₆H₄-4-F CH₂F 288 CH₃4-OCH₂C₆H₄-4-F CHF₂ 289 CH₃ 4-OCH₂C₆H₄-4-F CH₂CF₃ 290 CH₃ 4-OCH₂C₆H₄-4-FCH₂CH═CH₂ 291 CH₃ 4-OCH₂C₆H₄-4-F CH₂CH═CHCH₃ 292 CH₃ 4-OCH₂C₆H₄-4-FCH₂CH═C(CH₃)₂ 293 CH₃ 4-OCH₂C₆H₄-4-F CH₂CH═CHCl 294 CH₃ 4-OCH₂C₆H₄-4-FCH₂CH═CCl₂ 295 CH₃ 4-OCH₂C₆H₄-4-F CH₂C(CH₃)═CH₂ 296 CH₃ 4-OCH₂C₆H₄-4-FCH₂C≡CH 297 CH₃ 4-OCH₂C₆H₄-4-F CH₂Si(CH₃)₃ 298 CH₃ 4-OCH₂C₆H₄-4-FCH₂-c.propyl-2,2-Cl₂ 299 CH₃ 4-OCH₂C₆H₄-4-F CH₂CN 300 CH₃ 4-OCH₂C₆H₄-4-FCH₂COOC₂H₅ 301 CH₃ 4-OCH₂C₆H₄-4-F CH(CH₃)COOC₂H₅ 302 CH₃ 4-OCH₂C₆H₄-4-FCH₂C₆H₄-3-CF₃ 303 CH₃ 4-OCH₂C₆H₄-4-F CH₂C₆H₄-4-F 304 CH₃ 4-OCH₂C₆H₄-4-FCH₂C₆H₄-3-F 305 CH₃ 4-OCH₂C₆H₄-4-F CH₂C₆H₄-2-F 306 CH₃ 4-OCH₂C₆H₄-4-FC(═O)OC₂H₅ 307 CH₃ 4-OCH₂C₆H₄-4-F C(═O)NHCH₃ 308 CH₃ 4-OCH₂C₆H₄-4-FC(═O)C(═O)OC₂H₅ 309 CH₃ 4-OC₆H₄-3-CF₃ CH₃ 310 CH₃ 4-OC₆H₄-3-CF₃ C₂H₅ 311CH₃ 4-OC₆H₄-3-CF₃ n-C₃H₇ 312 CH₃ 4-OC₆H₄-3-CF₃ i-C₃H₇ 313 CH₃4-OC₆H₄-3-CF₃ n-C₄H₉ 314 CH₃ 4-OC₆H₄-3-CF₃ n-C₆H₁₃ 315 CH₃ 4-OC₆H₄-3-CF₃CH₂F 316 CH₃ 4-OC₆H₄-3-CF₃ CHF₂ 317 CH₃ 4-OC₆H₄-3-CF₃ CH₂CF₃ 318 CH₃4-OC₆H₄-3-CF₃ CH₂CH═CH₂ 319 CH₃ 4-OC₆H₄-3-CF₃ CH₂CH═CHCH₃ 320 CH₃4-OC₆H₄-3-CF₃ CH₂CH═C(CH₃)₂ 321 CH₃ 4-OC₆H₄-3-CF₃ CH₂CH═CHCl 322 CH₃4-OC₆H₄-3-CF₃ CH₂CH═CCl₂ 323 CH₃ 4-OC₆H₄-3-CF₃ CH₂C(CH₃)═CH₂ 324 CH₃4-OC₆H₄-3-CF₃ CH₂C≡CH 325 CH₃ 4-OC₆H₄-3-CF₃ CH₂Si(CH₃)₃ 326 CH₃4-OC₆H₄-3-CF₃ CH₂-c.propyl-2,2-Cl₂ 327 CH₃ 4-OC₆H₄-3-CF₃ CH₂CN 328 CH₃4-OC₆H₄-3-CF₃ CH₂COOC₂H₅ 329 CH₃ 4-OC₆H₄-3-CF₃ CH(CH₃)COOC₂H₅ 330 CH₃4-OC₆H₄-3-CF₃ CH₂C₆H₄-3-CF₃ 331 CH₃ 4-OC₆H₄-3-CF₃ CH₂C₆H₄-4-F 332 CH₃4-OC₆H₄-3-CF₃ CH₂C₆H₄-3-F 333 CH₃ 4-OC₆H₄-3-CF₃ CH₂C₆H₄-2-F 334 CH₃4-OC₆H₄-3-CF₃ C(═O)OC₂H₅ 335 CH₃ 4-OC₆H₄-3-CF₃ C(═O)NHCH₃ 336 CH₃4-OC₆H₄-3-CF₃ C(═O)C(═O)OC₂H₅ 337 C₂H₅ 4-OCH₂C₆H₄-3-CF₃ CH₃ 338 C₂H₅4-OCH₂C₆H₄-3-CF₃ C₂H₅ 339 C₂H₅ 4-OCH₂C₆H₄-3-CF₃ n-C₃H₇ 340 C₂H₅4-OCH₂C₆H₄-3-CF₃ i-C₃H₇ 341 C₂H₅ 4-OCH₂C₆H₄-3-CF₃ n-C₄H₉ 342 C₂H₅4-OCH₂C₆H₄-3-CF₃ n-C₆H₁₃ 343 C₂H₅ 4-OCH₂C₆H₄-3-CF₃ CH₂F 344 C₂H₅4-OCH₂C₆H₄-3-CF₃ CHF₂ 345 C₂H₅ 4-OCH₂C₆H₄-3-CF₃ CH₂CF₃ 346 C₂H₅4-OCH₂C₆H₄-3-CF₃ CH₂CH═CH₂ 347 C₂H₅ 4-OCH₂C₆H₄-3-CF₃ CH₂CH═CHCH₃ 348C₂H₅ 4-OCH₂C₆H₄-3-CF₃ CH₂CH═C(CH₃)₂ 349 C₂H₅ 4-OCH₂C₆H₄-3-CF₃ CH₂CH═CHCl350 C₂H₅ 4-OCH₂C₆H₄-3-CF₃ CH₂CH═CCl₂ 351 C₂H₅ 4-OCH₂C₆H₄-3-CF₃CH₂C(CH₃)═CH₂ 352 C₂H₅ 4-OCH₂C₆H₄-3-CF₃ CH₂C≡CH 353 C₂H₅4-OCH₂C₆H₄-3-CF₃ CH₂Si(CH₃)₃ 354 C₂H₅ 4-OCH₂C₆H₄-3-CF₃CH₂-c.propyl-2,2-Cl₂ 355 C₂H₅ 4-OCH₂C₆H₄-3-CF₃ CH₂CN 356 C₂H₅4-OCH₂C₆H₄-3-CF₃ CH₂COOC₂H₅ 357 C₂H₅ 4-OCH₂C₆H₄-3-CF₃ CH(CH₃)COOC₂H₅ 358C₂H₅ 4-OCH₂C₆H₄-3-CF₃ CH₂C₆H₄-3-CF₃ 359 C₂H₅ 4-OCH₂C₆H₄-3-CF₃CH₂C₆H₄-4-F 360 C₂H₅ 4-OCH₂C₆H₄-3-CF₃ CH₂C₆H₄-3-F 361 C₂H₅4-OCH₂C₆H₄-3-CF₃ CH₂C₆H₄-2-F 362 C₂H₅ 4-OC₆H₄-3-CF₃ C(═O)OC₂H₅ 363 C₂H₅4-OCH₂C₆H₄-3-CF₃ C(═O)NHCH₃ 364 C₂H₅ 4-OCH₂C₆H₄-3-CF₃ C(═O)C(═O)OC₂H₅365 CH₃ 4-OC₆H₄-4-Cl CH₃ 366 CH₃ 4-OC₆H₄-4-Cl C₂H₅ 367 CH₃ 4-OC₆H₄-4-Cln-C₃H₇ 368 CH₃ 4-OC₆H₄-4-Cl i-C₃H₇ 369 CH₃ 4-OC₆H₄-4-Cl n-C₄H₉ 370 CH₃4-OC₆H₄-4-Cl n-C₆H₁₃ 371 CH₃ 4-OC₆H₄-4-Cl CH₂F 372 CH₃ 4-OC₆H₄-4-Cl CHF₂373 CH₃ 4-OC₆H₄-4-Cl CH₂CF₃ 374 CH₃ 4-OC₆H₄-4-Cl CH₂CH═CH₂ 375 CH₃4-OC₆H₄-4-Cl CH₂CH═CHCH₃ 376 CH₃ 4-OC₆H₄-4-Cl CH₂CH═C(CH₃)₂ 377 CH₃4-OC₆H₄-4-Cl CH₂CH═CHCl 378 CH₃ 4-OC₆H₄-4-Cl CH₂CH═CCl₂ 379 CH₃4-OC₆H₄-4-Cl CH₂C(CH₃)═CH₂ 380 CH₃ 4-OC₆H₄-4-Cl CH₂C≡CH 381 CH₃4-OC₆H₄-4-Cl CH₂Si(CH₃)₃ 382 CH₃ 4-OC₆H₄-4-Cl CH₂-c.propyl-2,2-Cl₂ 383CH₃ 4-OC₆H₄-4-Cl CH₂CN 384 CH₃ 4-OC₆H₄-4-Cl CH₂COOC₂H₅ 385 CH₃4-OC₆H₄-4-Cl CH(CH₃)COOC₂H₅ 386 CH₃ 4-OC₆H₄-4-Cl CH₂C₆H₄-3-CF₃ 387 CH₃4-OC₆H₄-4-Cl CH₂C₆H₄-4-F 388 CH₃ 4-OC₆H₄-4-Cl CH₂C₆H₄-3-F 389 CH₃4-OC₆H₄-4-Cl CH₂C₆H₄-2-F 390 CH₃ 4-OC₆H₄-4-Cl C(═O)OC₂H₅ 391 CH₃4-OC₆H₄-4-Cl C(═O)NHCH₃ 392 CH₃ 4-OC₆H₄-4-Cl C(═O)C(═O)OC₂H₅ 393 CH₃4-OC₆H₄-3-Cl CH₃ 394 CH₃ 4-OC₆H₄-3-Cl C₂H₅ 395 CH₃ 4-OC₆H₄-3-Cl n-C₃H₇396 CH₃ 4-OC₆H₄-3-Cl i-C₃H₇ 397 CH₃ 4-OC₆H₄-3-Cl n-C₄H₉ 398 CH₃4-OC₆H₄-3-Cl n-C₆H₁₃ 399 CH₃ 4-OC₆H₄-3-Cl CH₂F 400 CH₃ 4-OC₆H₄-3-Cl CHF₂401 CH₃ 4-OC₆H₄-3-Cl CH₂CF₃ 402 CH₃ 4-OC₆H₄-3-Cl CH₂CH═CH₂ 403 CH₃4-OC₆H₄-3-Cl CH₂CH═CHCH₃ 404 CH₃ 4-OC₆H₄-3-Cl CH₂CH═C(CH₃)₂ 405 CH₃4-OC₆H₄-3-Cl CH₂CH═CHCl 406 CH₃ 4-OC₆H₄-3-Cl CH₂CH═CCl₂ 407 CH₃4-OC₆H₄-3-Cl CH₂C(CH₃)═CH₂ 408 CH₃ 4-OC₆H₄-3-Cl CH₂C≡CH 409 CH₃4-OC₆H₄-3-Cl CH₂Si(CH₃)₃ 410 CH₃ 4-OC₆H₄-3-Cl CH₂-c.propyl-2,2-Cl₂ 411CH₃ 4-OC₆H₄-3-Cl CH₂CN 412 CH₃ 4-OC₆H₄-3-Cl CH₂COOC₂H₅ 413 CH₃4-OC₆H₄-3-Cl CH(CH₃)COOC₂H₅ 414 CH₃ 4-OC₆H₄-3-Cl CH₂C₆H₄-3-CF₃ 415 CH₃4-OC₆H₄-3-Cl CH₂C₆H₄-4-F 416 CH₃ 4-OC₆H₄-3-Cl CH₂C₆H₄-3-F 417 CH₃4-OC₆H₄-3-Cl CH₂C₆H₄-2-F 418 CH₃ 4-OC₆H₄-3-Cl C(═O)OC₂H₅ 419 CH₃4-OC₆H₄-3-Cl C(═O)NHCH₃ 420 CH₃ 4-OC₆H₄-3-Cl C(═O)C(═O)OC₂H₅ 421 CH₃4-OC₆H₄-2-Cl CH₃ 242 CH₃ 4-OC₆H₄-2-Cl C₂H₅ 423 CH₃ 4-OC₆H₄-2-Cl n-C₃H₇424 CH₃ 4-OC₆H₄-2-Cl i-C₃H₇ 425 CH₃ 4-OC₆H₄-2-Cl n-C₄H₉ 426 CH₃4-OC₆H₄-2-Cl n-C₆H₁₃ 427 CH₃ 4-OC₆H₄-2-Cl CH₂F 428 CH₃ 4-OC₆H₄-2-Cl CHF₂429 CH₃ 4-OC₆H₄-2-Cl CH₂CF₃ 430 CH₃ 4-OC₆H₄-2-Cl CH₂CH═CH₂ 431 CH₃4-OC₆H₄-2-Cl CH₂CH═CHCH₃ 432 CH₃ 4-OC₆H₄-2-Cl CH₂CH═C(CH₃)₂ 433 CH₃4-OC₆H₄-2-Cl CH₂CH═CHCl 434 CH₃ 4-OC₆H₄-2-Cl CH₂CH═CCl₂ 435 CH₃4-OC₆H₄-2-Cl CH₂C(CH₃)═CH₂ 436 CH₃ 4-OC₆H₄-2-Cl CH₂C≡CH 437 CH₃4-OC₆H₄-2-Cl CH₂Si(CH₃)₃ 438 CH₃ 4-OC₆H₄-2-Cl CH₂-c.propyl-2,2-Cl₂ 439CH₃ 4-OC₆H₄-2-Cl CH₂CN 440 CH₃ 4-OC₆H₄-2-Cl CH₂COOC₂H₅ 441 CH₃4-OC₆H₄-2-Cl CH(CH₃)COOC₂H₅ 442 CH₃ 4-OC₆H₄-2-Cl CH₂C₆H₄-3-CF₃ 443 CH₃4-OC₆H₄-2-Cl CH₂C₆H₄-4-F 444 CH₃ 4-OC₆H₄-2-Cl CH₂C₆H₄-3-F 445 CH₃4-OC₆H₄-2-Cl CH₂C₆H₄-2-F 446 CH₃ 4-OC₆H₄-2-Cl C(═O)OC₂H₅ 447 CH₃4-OC₆H₄-2-Cl C(═O)NHCH₃ 448 CH₃ 4-OC₆H₄-2-Cl C(═O)C(═O)OC₂H₅ 449 CH₃4-OC₆H₄-4-F CH₃ 450 CH₃ 4-OC₆H₄-4-F C₂H₅ 451 CH₃ 4-OC₆H₄-4-F n-C₃H₇ 452CH₃ 4-OC₆H₄-4-F i-C₃H₇ 453 CH₃ 4-OC₆H₄-4-F n-C₄H₉ 454 CH₃ 4-OC₆H₄-4-Fn-C₆H₁₃ 455 CH₃ 4-OC₆H₄-4-F CH₂F 456 CH₃ 4-OC₆H₄-4-F CHF₂ 457 CH₃4-OC₆H₄-4-F CH₂CF₃ 458 CH₃ 4-OC₆H₄-4-F CH₂CH═CH₂ 459 CH₃ 4-OC₆H₄-4-FCH₂CH═CHCH₃ 460 CH₃ 4-OC₆H₄-4-F CH₂CH═C(CH₃)₂ 461 CH₃ 4-OC₆H₄-4-FCH₂CH═CHCl 462 CH₃ 4-OC₆H₄-4-F CH₂CH═CCl₂ 463 CH₃ 4-OC₆H₄-4-FCH₂C(CH₃)═CH₂ 464 CH₃ 4-OC₆H₄-4-F CH₂C≡CH 465 CH₃ 4-OC₆H₄-4-FCH₂Si(CH₃)₃ 466 CH₃ 4-OC₆H₄-4-F CH₂-c.propyl-2,2-Cl₂ 467 CH₃ 4-OC₆H₄-4-FCH₂CN 468 CH₃ 4-OC₆H₄-4-F CH₂COOC₂H₅ 469 CH₃ 4-OC₆H₄-4-F CH(CH₃)COOC₂H₅470 CH₃ 4-OC₆H₄-4-F CH₂C₆H₄-3-CF₃ 471 CH₃ 4-OC₆H₄-4-F CH₂C₆H₄-4-F 472CH₃ 4-OC₆H₄-4-F CH₂C₆H₄-3-F 473 CH₃ 4-OC₆H₄-4-F CH₂C₆H₄-2-F 474 CH₃4-OC₆H₄-4-F C(═O)OC₂H₅ 475 CH₃ 4-OC₆H₄-4-F C(═O)NHCH₃ 476 CH₃4-OC₆H₄-4-F C(═O)C(═O)OC₂H₅ 477 CH₃ 4-OC₆H₄-3-F CH₃ 478 CH₃ 4-OC₆H₄-3-FC₂H₅ 479 CH₃ 4-OC₆H₄-3-F n-C₃H₇ 480 CH₃ 4-OC₆H₄-3-F i-C₃H₇ 481 CH₃4-OC₆H₄-3-F n-C₄H₉ 482 CH₃ 4-OC₆H₄-3-F n-C₆H₁₃ 483 CH₃ 4-OC₆H₄-3-F CH₂F484 CH₃ 4-OC₆H₄-3-F CHF₂ 485 CH₃ 4-OC₆H₄-3-F CH₂CF₃ 486 CH₃ 4-OC₆H₄-3-FCH₂CH═CH₂ 487 CH₃ 4-OC₆H₄-3-F CH₂CH═CHCH₃ 488 CH₃ 4-OC₆H₄-3-FCH₂CH═C(CH₃)₂ 489 CH₃ 4-OC₆H₄-3-F CH₂CH═CHCl 490 CH₃ 4-OC₆H₄-3-FCH₂CH═CCl₂ 491 CH₃ 4-OC₆H₄-3-F CH₂C(CH₃)═CH₂ 492 CH₃ 4-OC₆H₄-3-F CH₂C≡CH493 CH₃ 4-OC₆H₄-3-F CH₂Si(CH₃)₃ 494 CH₃ 4-OC₆H₄-3-F CH₂-c.propyl-2,2-Cl₂495 CH₃ 4-OC₆H₄-3-F CH₂CN 496 CH₃ 4-OC₆H₄-3-F CH₂COOC₂H₅ 497 CH₃4-OC₆H₄-3-F CH(CH₃)COOC₂H₅ 498 CH₃ 4-OC₆H₄-3-F CH₂C₆H₄-3-CF₃ 499 CH₃4-OC₆H₄-3-F CH₂C₆H₄-4-F 500 CH₃ 4-OC₆H₄-3-F CH₂C₆H₄-3-F 501 CH₃4-OC₆H₄-3-F CH₂C₆H₄-2-F 502 CH₃ 4-OC₆H₄-3-F C(═O)OC₂H₅ 503 CH₃4-OC₆H₄-3-F C(═O)NHCH₃ 504 CH₃ 4-OC₆H₄-3-F C(═O)C(═O)OC₂H₅ 505 CH₃4-OC₆H₄-2-F CH₃ 506 CH₃ 4-OC₆H₄-2-F C₂H₅ 507 CH₃ 4-OC₆H₄-2-F n-C₃H₇ 508CH₃ 4-OC₆H₄-2-F i-C₃H₇ 509 CH₃ 4-OC₆H₄-2-F n-C₄H₉ 510 CH₃ 4-OC₆H₄-2-Fn-C₆H₁₃ 511 CH₃ 4-OC₆H₄-2-F CH₂F 512 CH₃ 4-OC₆H₄-2-F CHF₂ 513 CH₃4-OC₆H₄-2-F CH₂CF₃ 514 CH₃ 4-OC₆H₄-2-F CH₂CH═CH₂ 515 CH₃ 4-OC₆H₄-2-FCH₂CH═CHCH₃ 516 CH₃ 4-OC₆H₄-2-F CH₂CH═C(CH₃)₂ 517 CH₃ 4-OC₆H₄-2-FCH₂CH═CHCl 518 CH₃ 4-OC₆H₄-2-F CH₂CH═CCl₂ 519 CH₃ 4-OC₆H₄-2-FCH₂C(CH₃)═CH₂ 520 CH₃ 4-OC₆H₄-2-F CH₂C≡CH 521 CH₃ 4-OC₆H₄-2-FCH₂Si(CH₃)₃ 522 CH₃ 4-OC₆H₄-2-F CH₂-c.propyl-2,2-Cl₂ 523 CH₃ 4-OC₆H₄-2-FCH₂CN 524 CH₃ 4-OC₆H₄-2-F CH₂COOC₂H₅ 525 CH₃ 4-OC₆H₄-2-F CH(CH₃)COOC₂H₅526 CH₃ 4-OC₆H₄-2-F CH₂C₆H₄-3-CF₃ 527 CH₃ 4-OC₆H₄-2-F CH₂C₆H₄-4-F 528CH₃ 4-OC₆H₄-2-F CH₂C₆H₄-3-F 529 CH₃ 4-OC₆H₄-2-F CH₂C₆H₄-2-F 530 CH₃4-OC₆H₄-2-F C(═O)OC₂H₅ 531 CH₃ 4-OC₆H₄-2-F C(═O)NHCH₃ 532 CH₃4-OC₆H₄-2-F C(═O)C(═O)OC₂H₅ 533 CH₃ 4-OC₆H₄-4-Br CH₃ 534 CH₃4-OC₆H₄-4-Br C₂H₅ 535 CH₃ 4-OC₆H₄-4-Br n-C₃H₇ 536 CH₃ 4-OC₆H₄-4-Bri-C₃H₇ 537 CH₃ 4-OC₆H₄-4-Br n-C₄H₉ 538 CH₃ 4-OC₆H₄-4-Br n-C₆H₁₃ 539 CH₃4-OC₆H₄-4-Br CH₂F 540 CH₃ 4-OC₆H₄-4-Br CHF₂ 541 CH₃ 4-OC₆H₄-4-Br CH₂CF₃542 CH₃ 4-OC₆H₄-4-Br CH₂CH═CH₂ 543 CH₃ 4-OC₆H₄-4-Br CH₂CH═CHCH₃ 544 CH₃4-OC₆H₄-4-Br CH₂CH═C(CH₃)₂ 545 CH₃ 4-OC₆H₄-4-Br CH₂CH═CHCl 546 CH₃4-OC₆H₄-4-Br CH₂CH═CCl₂ 547 CH₃ 4-OC₆H₄-4-Br CH₂C(CH₃)═CH₂ 548 CH₃4-OC₆H₄-4-Br CH₂C≡CH 549 CH₃ 4-OC₆H₄-4-Br CH₂Si(CH₃)₃ 550 CH₃4-OC₆H₄-4-Br CH₂-c.propyl-2,2-Cl₂ 551 CH₃ 4-OC₆H₄-4-Br CH₂CN 552 CH₃4-OC₆H₄-4-Br CH₂COOC₂H₅ 553 CH₃ 4-OC₆H₄-4-Br CH(CH₃)COOC₂H₅ 554 CH₃4-OC₆H₄-4-Br CH₂C₆H₄-3-CF₃ 555 CH₃ 4-OC₆H₄-4-Br CH₂C₆H₄-4-F 556 CH₃4-OC₆H₄-4-Br CH₂C₆H₄-3-F 557 CH₃ 4-OC₆H₄-4-Br CH₂C₆H₄-2-F 558 CH₃4-OC₆H₄-4-Br C(═O)OC₂H₅ 559 CH₃ 4-OC₆H₄-4-Br C(═O)NHCH₃ 560 CH₃4-OC₆H₄-4-Br C(═O)C(═O)OC₂H₅ 561 CH₃ 4-OC₆H₄-3-Br CH₃ 562 CH₃4-OC₆H₄-3-Br C₂H₅ 563 CH₃ 4-OC₆H₄-3-Br n-C₃H₇ 564 CH₃ 4-OC₆H₄-3-Bri-C₃H₇ 565 CH₃ 4-OC₆H₄-3-Br n-C₄H₉ 566 CH₃ 4-OC₆H₄-3-Br n-C₆H₁₃ 567 CH₃4-OC₆H₄-3-Br CH₂F 568 CH₃ 4-OC₆H₄-3-Br CHF₂ 569 CH₃ 4-OC₆H₄-3-Br CH₂CF₃570 CH₃ 4-OC₆H₄-3-Br CH₂CH═CH₂ 571 CH₃ 4-OC₆H₄-3-Br CH₂CH═CHCH₃ 572 CH₃4-OC₆H₄-3-Br CH₂CH═C(CH₃)₂ 573 CH₃ 4-OC₆H₄-3-Br CH₂CH═CHCl 574 CH₃4-OC₆H₄-3-Br CH₂CH═CCl₂ 575 CH₃ 4-OC₆H₄-3-Br CH₂C(CH₃)═CH₂ 576 CH₃4-OC₆H₄-3-Br CH₂C≡H 577 CH₃ 4-OC₆H₄-3-Br CH₂Si(CH₃)₃ 578 CH₃4-OC₆H₄-3-Br CH₂-c.propyl-2,2-Cl₂ 579 CH₃ 4-OC₆H₄-3-Br CH₂CN 580 CH₃4-OC₆H₄-3-Br CH₂COOC₂H₅ 581 CH₃ 4-OC₆H₄-3-Br CH(CH₃)COOC₂H₅ 582 CH₃4-OC₆H₄-3-Br CH₂C₆H₄-3-CF₃ 583 CH₃ 4-OC₆H₄-3-Br CH₂C₆H₄-4-F 584 CH₃4-OC₆H₄-3-Br CH₂C₆H₄-3-F 585 CH₃ 4-OC₆H₄-3-Br CH₂C₆H₄-2-F 586 CH₃4-OC₆H₄-3-Br C(═O)OC₂H₅ 587 CH₃ 4-OC₆H₄-3-Br C(═O)NHCH₃ 588 CH₃4-OC₆H₄-3-Br C(═O)C(═O)OC₂H₅ 589 CH₃ 4-OC₆H₄-2-Br CH₃ 590 CH₃4-OC₆H₄-2-Br C₂H₅ 591 CH₃ 4-OC₆H₄-2-Br n-C₃H₇ 592 CH₃ 4-OC₆H₄-2-Bri-C₃H₇ 593 CH₃ 4-OC₆H₄-2-Br n-C₄H₉ 594 CH₃ 4-OC₆H₄-2-Br n-C₆H₁₃ 595 CH₃4-OC₆H₄-2-Br CH₂F 596 CH₃ 4-OC₆H₄-2-Br CHF₂ 597 CH₃ 4-OC₆H₄-2-Br CH₂CF₃598 CH₃ 4-OC₆H₄-2-Br CH₂CH═CH₂ 599 CH₃ 4-OC₆H₄-2-Br CH₂CH═CHCH₃ 600 CH₃4-OC₆H₄-2-Br CH₂CH═C(CH₃)₂ 601 CH₃ 4-OC₆H₄-2-Br CH₂CH═CHCl 602 CH₃4-OC₆H₄-2-Br CH₂CH═CCl₂ 603 CH₃ 4-OC₆H₄-2-Br CH₂C(CH₃)═CH₂ 604 CH₃4-OC₆H₄-2-Br CH₂C≡CH 605 CH₃ 4-OC₆H₄-2-Br CH₂Si(CH₃)₃ 606 CH₃4-OC₆H₄-2-Br CH₂-c.propyl-2,2-Cl₂ 607 CH₃ 4-OC₆H₄-2-Br CH₂CN 608 CH₃4-OC₆H₄-2-Br CH₂COOC₂H₅ 609 CH₃ 4-OC₆H₄-2-Br CH(CH₃)COOC₂H₅ 610 CH₃4-OC₆H₄-2-Br CH₂C₆H₄-3-CF₃ 611 CH₃ 4-OC₆H₄-2-Br CH₂C₆H₄-4-F 612 CH₃4-OC₆H₄-2-Br CH₂C₆H₄-3-F 613 CH₃ 4-OC₆H₄-2-Br CH₂C₆H₄-2-F 614 CH₃4-OC₆H₄-2-Br C(═O)OC₂H₅ 615 CH₃ 4-OC₆H₄-2-Br C(═O)NHCH₃ 616 CH₃4-OC₆H₄-2-Br C(═O)C(═O)OC₂H₅ 617 CH₃ 4-OC₆H₃-2,4-Cl₂ CH₃ 618 CH₃4-OC₆H₃-2,4-Cl₂ C₂H₅ 619 CH₃ 4-OC₆H₃-2,4-Cl₂ n-C₃H₇ 620 CH₃4-OC₆H₃-2,4-Cl₂ i-C₃H₇ 621 CH₃ 4-OC₆H₃-2,4-Cl₂ n-C₄H₉ 622 CH₃4-OC₆H₃-2,4-Cl₂ n-C₆H₁₃ 623 CH₃ 4-OC₆H₃-2,4-Cl₂ CH₂F 624 CH₃4-OC₆H₃-2,4-Cl₂ CHF₂ 625 CH₃ 4-OC₆H₃-2,4-Cl₂ CH₂CF₃ 626 CH₃4-OC₆H₃-2,4-Cl₂ CH₂CH═CH₂ 627 CH₃ 4-OC₆H₃-2,4-Cl₂ CH₂CH═CHCH₃ 628 CH₃4-OC₆H₃-2,4-Cl₂ CH₂CH═C(CH₃)₂ 629 CH₃ 4-OC₆H₃-2,4-Cl₂ CH₂CH═CHCl 630 CH₃4-OC₆H₃-2,4-Cl₂ CH₂CH═CCl₂ 631 CH₃ 4-OC₆H₃-2,4-Cl₂ CH₂C(CH₃)═CH₂ 632 CH₃4-OC₆H₃-2,4-Cl₂ CH₂C≡H 633 CH₃ 4-OC₆H₃-2,4-Cl₂ CH₂Si(CH₃)₃ 634 CH₃4-OC₆H₃-2,4-Cl₂ CH₂-c.propyl-2,2-Cl₂ 635 CH₃ 4-OC₆H₃-2,4-Cl₂ CH₂CN 636CH₃ 4-OC₆H₃-2,4-Cl₂ CH₂COOC₂H₅ 637 CH₃ 4-OC₆H₃-2,4-Cl₂ CH(CH₃)COOC₂H₅638 CH₃ 4-OC₆H₃-2,4-Cl₂ CH₂C₆H₄-3-CF₃ 639 CH₃ 4-OC₆H₃-2,4-Cl₂CH₂C₆H₄-4-F 640 CH₃ 4-OC₆H₃-2,4-Cl₂ CH₂C₆H₄-3-F 641 CH₃ 4-OC₆H₃-2,4-Cl₂CH₂C₆H₄-2-F 642 CH₃ 4-OC₆H₃-2,4-Cl₂ C(═O)OC₂H₅ 643 CH₃ 4-OC₆H₃-2,4-Cl₂C(═O)NHCH₃ 644 CH₃ 4-OC₆H₃-2,4-Cl₂ C(═O)C(═O)OC₂H₅ 645 CH₃4-OC₆H₃-3,4-Cl₂ CH₃ 646 CH₃ 4-OC₆H₃-3,4-Cl₂ C₂H₅ 647 CH₃ 4-OC₆H₃-3,4-Cl₂n-C₃H₇ 648 CH₃ 4-OC₆H₃-3,4-Cl₂ i-C₃H₇ 649 CH₃ 4-OC₆H₃-3,4-Cl₂ n-C₄H₉ 650CH₃ 4-OC₆H₃-3,4-Cl₂ n-C₆H₁₃ 651 CH₃ 4-OC₆H₃-3,4-Cl₂ CH₂F 652 CH₃4-OC₆H₃-3,4-Cl₂ CHF₂ 653 CH₃ 4-OC₆H₃-3,4-Cl₂ CH₂CF₃ 654 CH₃4-OC₆H₃-3,4-Cl₂ CH₂CH═CH₂ 655 CH₃ 4-OC₆H₃-3,4-Cl₂ CH₂CH═CHCH₃ 656 CH₃4-OC₆H₃-3,4-Cl₂ CH₂CH═C(CH₃)₂ 657 CH₃ 4-OC₆H₃-3,4-Cl₂ CH₂CH═CHCl 658 CH₃4-OC₆H₃-3,4-Cl₂ CH₂CH═CCl₂ 659 CH₃ 4-OC₆H₃-3,4-Cl₂ CH₂C(CH₃)═CH₂ 660 CH₃4-OC₆H₃-3,4-Cl₂ CH₂C≡CH 661 CH₃ 4-OC₆H₃-3,4-Cl₂ CH₂Si(CH₃)₃ 662 CH₃4-OC₆H₃-3,4-Cl₂ CH₂-c.propyl-2,2-Cl₂ 663 CH₃ 4-OC₆H₃-3,4-Cl₂ CH₂CN 664CH₃ 4-OC₆H₃-3,4-Cl₂ CH₂COOC₂H₅ 665 CH₃ 4-OC₆H₃-3,4-Cl₂ CH(CH₃)COOC₂H₅666 CH₃ 4-OC₆H₃-3,4-Cl₂ CH₂C₆H₄-3-CF₃ 667 CH₃ 4-OC₆H₃-3,4-Cl₂CH₂C₆H₄-4-F 668 CH₃ 4-OC₆H₃-3,4-Cl₂ CH₂C₆H₄-3-F 669 CH₃ 4-OC₆H₃-3,4-Cl₂CH₂C₆H₄-2-F 670 CH₃ 4-OC₆H₃-3,4-Cl₂ C(═O)OC₂H₅ 671 CH₃ 4-OC₆H₃-3,4-Cl₂C(═O)NHCH₃ 672 CH₃ 4-OC₆H₃-3,4-Cl₂ C(═O)C(═O)OC₂H₅ 673 CH₃ 4-OC₆H₃-2-Cl,4-Br CH₃ 674 CH₃ 4-OC₆H₃-2-Cl, 4-Br C₂H₅ 675 CH₃ 4-OC₆H₃-2-Cl, 4-Brn-C₃H₇ 676 CH₃ 4-OC₆H₃-2-Cl, 4-Br i-C₃H₇ 677 CH₃ 4-OC₆H₃-2-Cl, 4-Brn-C₄H₉ 678 CH₃ 4-OC₆H₃-2-Cl, 4-Br n-C₆H₁₃ 679 CH₃ 4-OC₆H₃-2-Cl, 4-BrCH₂F 680 CH₃ 4-OC₆H₃-2-Cl, 4-Br CHF₂ 681 CH₃ 4-OC₆H₃-2-Cl, 4-Br CH₂CF₃682 CH₃ 4-OC₆H₃-2-Cl, 4-Br CH₂CH═CH₂ 683 CH₃ 4-OC₆H₃-2-Cl, 4-BrCH₂CH═CHCH₃ 684 CH₃ 4-OC₆H₃-2-Cl, 4-Br CH₂CH═C(CH₃)₂ 685 CH₃4-OC₆H₃-2-Cl, 4-Br CH₂CH═CHCl 686 CH₃ 4-OC₆H₃-2-Cl, 4-Br CH₂CH═CCl₂ 687CH₃ 4-OC₆H₃-2-Cl, 4-Br CH₂C(CH₃)═CH₂ 688 CH₃ 4-OC₆H₃-2-Cl, 4-Br CH₂C≡CH689 CH₃ 4-OC₆H₃-2-Cl, 4-Br CH₂Si(CH₃)₃ 690 CH₃ 4-OC₆H₃-2-Cl, 4-BrCH₂-c.propyl-2,2-Cl₂ 691 CH₃ 4-OC₆H₃-2-Cl, 4-Br CH₂CN 692 CH₃4-OC₆H₃-2-Cl, 4-Br CH₂COOC₂H₅ 693 CH₃ 4-OC₆H₃-2-Cl, 4-Br CH(CH₃)COOC₂H₅694 CH₃ 4-OC₆H₃-2-Cl, 4-Br CH₂C₆H₄-3-CF₃ 695 CH₃ 4-OC₆H₃-2-Cl, 4-BrCH₂C₆H₄-4-F 696 CH₃ 4-OC₆H₃-2-Cl, 4-Br CH₂C₆H₄-3-F 697 CH₃ 4-OC₆H₃-2-Cl,4-Br CH₂C₆H₄-2-F 698 CH₃ 4-OC₆H₃-2-Cl, 4-Br C(═O)OC₂H₅ 699 CH₃4-OC₆H₃-2-Cl, 4-Br C(═O)NHCH₃ 700 CH₃ 4-OC₆H₃-2-Cl, 4-Br C(═O)C(═O)OC₂H₅701 CH₃ 4-OC₆H₃-3,4-(—OCH₂O—) CH₃ 702 CH₃ 4-OC₆H₃-3,4-(—OCH₂O—) C₂H₅ 703CH₃ 4-OC₆H₃-3,4-(—OCH₂O—) n-C₃H₇ 704 CH₃ 4-OC₆H₃-3,4-(—OCH₂O—) i-C₃H₇705 CH₃ 4-OC₆H₃-3,4-(—OCH₂O—) n-C₄H₉ 706 CH₃ 4-OC₆H₃-3,4-(—OCH₂O—)n-C₆H₁₃ 707 CH₃ 4-OC₆H₃-3,4-(—OCH₂O—) CH₂F 708 CH₃ 4-OC₆H₃-3,4-(—OCH₂O—)CHF₂ 709 CH₃ 4-OC₆H₃-3,4-(—OCH₂O—) CH₂CF₃ 710 CH₃ 4-OC₆H₃-3,4-(—OCH₂O—)CH₂CH═CH₂ 711 CH₃ 4-OC₆H₃-3,4-(—OCH₂O—) CH₂CH═CHCH₃ 712 CH₃4-OC₆H₃-3,4-(—OCH₂O—) CH₂CH═C(CH₃)₂ 713 CH₃ 4-OC₆H₃-3,4-(—OCH₂O—)CH₂CH═CHCl 714 CH₃ 4-OC₆H₃-3,4-(—OCH₂O—) CH₂CH═CCl₂ 715 CH₃4-OC₆H₃-3,4-(—OCH₂O—) CH₂C(CH₃)═CH₂ 716 CH₃ 4-OC₆H₃-3,4-(—OCH₂O—)CH₂C≡CH 717 CH₃ 4-OC₆H₃-3,4-(—OCH₂O—) CH₂Si(CH₃)₃ 718 CH₃4-OC₆H₃-3,4-(—OCH₂O—) CH₂-c.propyl-2,2-Cl₂ 719 CH₃ 4-OC₆H₃-3,4-(—OCH₂O—)CH₂CN 720 CH₃ 4-OC₆H₃-3,4-(—OCH₂O—) CH₂COOC₂H₅ 721 CH₃4-OC₆H₃-3,4-(—OCH₂O—) CH(CH₃)COOC₂H₅ 722 CH₃ 4-OC₆H₃-3,4-(—OCH₂O—)CH₂C₆H₄-3-CF₃ 723 CH₃ 4-OC₆H₃-3,4-(—OCH₂O—) CH₂C₆H₄-4-F 724 CH₃4-OC₆H₃-3,4-(—OCH₂O—) CH₂C₆H₄-3-F 725 CH₃ 4-OC₆H₃-3,4-(—OCH₂O—)CH₂C₆H₄-2-F 726 CH₃ 4-OC₆H₃-3,4-(—OCH₂O—) C(═O)OC₂H₅ 727 CH₃4-OC₆H₃-3,4-(—OCH₂O—) C(═O)NHCH₃ 728 CH₃ 4-OC₆H₃-3,4-(—OCH₂O—)C(═O)C(═O)OC₂H₅ 729 CH₃ 4-OC₆H₄-4-SCH₃ CH₃ 730 CH₃ 4-OC₆H₄-4-SCH₃ C₂H₅731 CH₃ 4-OC₆H₄-4-SCH₃ n-C₃H₇ 732 CH₃ 4-OC₆H₄-4-SCH₃ i-C₃H₇ 733 CH₃4-OC₆H₄-4-SCH₃ n-C₄H₉ 734 CH₃ 4-OC₆H₄-4-SCH₃ n-C₆H₁₃ 735 CH₃4-OC₆H₄-4-SCH₃ CH₂F 736 CH₃ 4-OC₆H₄-4-SCH₃ CHF₂ 737 CH₃ 4-OC₆H₄-4-SCH₃CH₂CF₃ 738 CH₃ 4-OC₆H₄-4-SCH₃ CH₂CH═CH₂ 739 CH₃ 4-OC₆H₄-4-SCH₃CH₂CH═CHCH₃ 740 CH₃ 4-OC₆H₄-4-SCH₃ CH₂CH═C(CH₃)₂ 741 CH₃ 4-OC₆H₄-4-SCH₃CH₂CH═CHCl 742 CH₃ 4-OC₆H₄-4-SCH₃ CH₂CH═CCl₂ 743 CH₃ 4-OC₆H₄-4-SCH₃CH₂C(CH₃)═CH₂ 744 CH₃ 4-OC₆H₄-4-SCH₃ CH₂C≡CH 745 CH₃ 4-OC₆H₄-4-SCH₃CH₂Si(CH₃)₃ 746 CH₃ 4-OC₆H₄-4-SCH₃ CH₂-c.propyl-2,2-Cl₂ 747 CH₃4-OC₆H₄-4-SCH₃ CH₂CN 748 CH₃ 4-OC₆H₄-4-SCH₃ CH₂COOC₂H₅ 749 CH₃4-OC₆H₄-4-SCH₃ CH(CH₃)COOC₂H₅ 750 CH₃ 4-OC₆H₄-4-SCH₃ CH₂C₆H₄-3-CF₃ 751CH₃ 4-OC₆H₄-4-SCH₃ CH₂C₆H₄-4-F 752 CH₃ 4-OC₆H₄-4-SCH₃ CH₂C₆H₄-3-F 753CH₃ 4-OC₆H₄-4-SCH₃ CH₂C₆H₄-2-F 754 CH₃ 4-OC₆H₄-4-SCH₃ C(═O)OC₂H₅ 755 CH₃4-OC₆H₄-4-SCH₃ C(═O)NHCH₃ 756 CH₃ 4-OC₆H₄-4-SCH₃ C(═O)C(═O)OC₂H₅ 757 CH₃4-OC₆H₄-4-OCH₃ CH₃ 758 CH₃ 4-OC₆H₄-4-OCH₃ C₂H₅ 759 CH₃ 4-OC₆H₄-4-OCH₃n-C₃H₇ 760 CH₃ 4-OC₆H₄-4-OCH₃ i-C₃H₇ 761 CH₃ 4-OC₆H₄-4-OCH₃ n-C₄H₉ 762CH₃ 4-OC₆H₄-4-OCH₃ n-C₆H₁₃ 763 CH₃ 4-OC₆H₄-4-OCH₃ CH₂F 764 CH₃4-OC₆H₄-4-OCH₃ CHF₂ 765 CH₃ 4-OC₆H₄-4-OCH₃ CH₂CF₃ 766 CH₃ 4-OC₆H₄-4-OCH₃CH₂CH═CH₂ 767 CH₃ 4-OC₆H₄-4-OCH₃ CH₂CH═CHCH₃ 768 CH₃ 4-OC₆H₄-4-OCH₃CH₂CH═C(CH₃)₂ 769 CH₃ 4-OC₆H₄-4-OCH₃ CH₂CH═CHCl 770 CH₃ 4-OC₆H₄-4-OCH₃CH₂CH═CCl₂ 771 CH₃ 4-OC₆H₄-4-OCH₃ CH₂C(CH₃)═CH₂ 772 CH₃ 4-OC₆H₄-4-OCH₃CH₂C≡CH 773 CH₃ 4-OC₆H₄-4-OCH₃ CH₂Si(CH₃)₃ 774 CH₃ 4-OC₆H₄-4-OCH₃CH₂-c.propyl-2,2-Cl₂ 775 CH₃ 4-OC₆H₄-4-OCH₃ CH₂CN 776 CH₃ 4-OC₆H₄-4-OCH₃CH₂COOC₂H₅ 777 CH₃ 4-OC₆H₄-4-OCH₃ CH(CH₃)COOC₂H₅ 778 CH₃ 4-OC₆H₄-4-OCH₃CH₂C₆H₄-3-CF₃ 779 CH₃ 4-OC₆H₄-4-OCH₃ CH₂C₆H₄-4-F 780 CH₃ 4-OC₆H₄-4-OCH₃CH₂C₆H₄-3-F 781 CH₃ 4-OC₆H₄-4-OCH₃ CH₂C₆H₄-2-F 782 CH₃ 4-OC₆H₄-4-OCH₃C(═O)OC₂H₅ 783 CH₃ 4-OC₆H₄-4-OCH₃ C(═O)NHCH₃ 784 CH₃ 4-OC₆H₄-4-OCH₃C(═O)C(═O)OC₂H₅ 785 CH₃ 4-OC₆H₄-4-t-butyl CH₃ 786 CH₃ 4-OC₆H₄-4-t-butylC₂H₅ 787 CH₃ 4-OC₆H₄-4-t-butyl n-C₃H₇ 788 CH₃ 4-OC₆H₄-4-t-butyl i-C₃H₇789 CH₃ 4-OC₆H₄-4-t-butyl n-C₄H₉ 790 CH₃ 4-OC₆H₄-4-t-butyl n-C₆H₁₃ 791CH₃ 4-OC₆H₄-4-t-butyl CH₂F 792 CH₃ 4-OC₆H₄-4-t-butyl CHF₂ 793 CH₃4-OC₆H₄-4-t-butyl CH₂CF₃ 794 CH₃ 4-OC₆H₄-4-t-butyl CH₂CH═CH₂ 795 CH₃4-OC₆H₄-4-t-butyl CH₂CH═CHCH₃ 796 CH₃ 4-OC₆H₄-4-t-butyl CH₂CH═C(CH₃)₂797 CH₃ 4-OC₆H₄-4-t-butyl CH₂CH═CHCl 798 CH₃ 4-OC₆H₄-4-t-butylCH₂CH═CCl₂ 799 CH₃ 4-OC₆H₄-4-t-butyl CH₂C(CH₃)═CH₂ 800 CH₃4-OC₆H₄-4-t-butyl CH₂C≡CH 801 CH₃ 4-OC₆H₄-4-t-butyl CH₂Si(CH₃)₃ 802 CH₃4-OC₆H₄-4-t-butyl CH₂-c.propyl-2,2-Cl₂ 803 CH₃ 4-OC₆H₄-4-t-butyl CH₂CN804 CH₃ 4-OC₆H₄-4-t-butyl CH₂COOC₂H₅ 805 CH₃ 4-OC₆H₄-4-t-butylCH(CH₃)COOC₂H₅ 806 CH₃ 4-OC₆H₄-4-t-butyl CH₂C₆H₄-3-CF₃ 807 CH₃4-OC₆H₄-4-t-butyl CH₂C₆H₄-4-F 808 CH₃ 4-OC₆H₄-4-t-butyl CH₂C₆H₄-3-F 809CH₃ 4-OC₆H₄-4-t-butyl CH₂C₆H₄-2-F 810 CH₃ 4-OC₆H₄-4-t-butyl C(═O)OC₂H₅811 CH₃ 4-OC₆H₄-4-t-butyl C(═O)NHCH₃ 812 CH₃ 4-OC₆H₄-4-t-butylC(═O)C(═O)OC₂H₅ 813 CH₃ 4-OC₆H₄-4-CF₃ CH₃ 814 CH₃ 4-OC₆H₄-4-CF₃ C₂H₅ 815CH₃ 4-OC₆H₄-4-CF₃ n-C₃H₇ 816 CH₃ 4-OC₆H₄-4-CF₃ i-C₃H₇ 817 CH₃4-OC₆H₄-4-CF₃ n-C₄H₉ 818 CH₃ 4-OC₆H₄-4-CF₃ n-C₆H₁₃ 819 CH₃ 4-OC₆H₄-4-CF₃CH₂F 820 CH₃ 4-OC₆H₄-4-CF₃ CHF₂ 821 CH₃ 4-OC₆H₄-4-CF₃ CH₂CF₃ 822 CH₃4-OC₆H₄-4-CF₃ CH₂CH═CH₂ 823 CH₃ 4-OC₆H₄-4-CF₃ CH₂CH═CHCH₃ 824 CH₃4-OC₆H₄-4-CF₃ CH₂CH═C(CH₃)₂ 825 CH₃ 4-OC₆H₄-4-CF₃ CH₂CH═CHCl 826 CH₃4-OC₆H₄-4-CF₃ CH₂CH═CCl₂ 827 CH₃ 4-OC₆H₄-4-CF₃ CH₂C(CH₃)═CH₂ 828 CH₃4-OC₆H₄-4-CF₃ CH₂C≡CH 829 CH₃ 4-OC₆H₄-4-CF₃ CH₂Si(CH₃)₃ 830 CH₃4-OC₆H₄-4-CF₃ CH₂-c.propyl-2,2-Cl₂ 831 CH₃ 4-OC₆H₄-4-CF₃ CH₂CN 832 CH₃4-OC₆H₄-4-CF₃ CH₂COOC₂H₅ 833 CH₃ 4-OC₆H₄-4-CF₃ CH(CH₃)COOC₂H₅ 834 CH₃4-OC₆H₄-4-CF₃ CH₂C₆H₄-3-CF₃ 835 CH₃ 4-OC₆H₄-4-CF₃ CH₂C₆H₄-4-F 836 CH₃4-OC₆H₄-4-CF₃ CH₂C₆H₄-3-F 837 CH₃ 4-OC₆H₄-4-CF₃ CH₂C₆H₄-2-F 838 CH₃4-OC₆H₄-4-CF₃ C(═O)OC₂H₅ 839 CH₃ 4-OC₆H₄-4-CF₃ C(═O)NHCH₃ 840 CH₃4-OC₆H₄-4-CF₃ C(═O)C(═O)OC₂H₅ 841 CH₃ 4-OC₆H₄-2-CF₃ CH₃ 842 CH₃4-OC₆H₄-2-CF₃ C₂H₅ 843 CH₃ 4-OC₆H₄-2-CF₃ n-C₃H₇ 844 CH₃ 4-OC₆H₄-2-CF₃i-C₃H₇ 845 CH₃ 4-OC₆H₄-2-CF₃ n-C₄H₉ 846 CH₃ 4-OC₆H₄-2-CF₃ n-C₆H₁₃ 847CH₃ 4-OC₆H₄-2-CF₃ CH₂F 848 CH₃ 4-OC₆H₄-2-CF₃ CHF₂ 849 CH₃ 4-OC₆H₄-2-CF₃CH₂CF₃ 850 CH₃ 4-OC₆H₄-2-CF₃ CH₂CH═CH₂ 851 CH₃ 4-OC₆H₄-2-CF₃ CH₂CH═CHCH₃852 CH₃ 4-OC₆H₄-2-CF₃ CH₂CH═C(CH₃)₂ 853 CH₃ 4-OC₆H₄-2-CF₃ CH₂CH═CHCl 854CH₃ 4-OC₆H₄-2-CF₃ CH₂CH═CCl₂ 855 CH₃ 4-OC₆H₄-2-CF₃ CH₂C(CH₃)═CH₂ 856 CH₃4-OC₆H₄-2-CF₃ CH₂C≡CH 857 CH₃ 4-OC₆H₄-2-CF₃ CH₂Si(CH₃)₃ 858 CH₃4-OC₆H₄-2-CF₃ CH₂-c.propyl-2,2-Cl₂ 859 CH₃ 4-OC₆H₄-2-CF₃ CH₂CN 860 CH₃4-OC₆H₄-2-CF₃ CH₂COOC₂H₅ 861 CH₃ 4-OC₆H₄-2-CF₃ CH(CH₃)COOC₂H₅ 862 CH₃4-OC₆H₄-2-CF₃ CH₂C₆H₄-3-CF₃ 863 CH₃ 4-OC₆H₄-2-CF₃ CH₂C₆H₄-4-F 864 CH₃4-OC₆H₄-2-CF₃ CH₂C₆H₄-3-F 865 CH₃ 4-OC₆H₄-2-CF₃ CH₂C₆H₄-2-F 866 CH₃4-OC₆H₄-2-CF₃ C(═O)OC₂H₅ 867 CH₃ 4-OC₆H₄-2-CF₃ C(═O)NHCH₃ 868 CH₃4-OC₆H₄-2-CF₃ C(═O)C(═O)OC₂H₅ 869 CH₃ 4-OCH₂C₆H₄-4-Cl CH₃ 870 CH₃4-OCH₂C₆H₄-4-Cl C₂H₅ 871 CH₃ 4-OCH₂C₆H₄-4-Cl n-C₃H₇ 872 CH₃4-OCH₂C₆H₄-4-Cl i-C₃H₇ 873 CH₃ 4-OCH₂C₆H₄-4-Cl n-C₄H₉ 874 CH₃4-OCH₂C₆H₄-4-Cl n-C₆H₁₃ 875 CH₃ 4-OCH₂C₆H₄-4-Cl CH₂F 876 CH₃4-OCH₂C₆H₄-4-Cl CHF₂ 877 CH₃ 4-OCH₂C₆H₄-4-Cl CH₂CF₃ 878 CH₃4-OCH₂C₆H₄-4-Cl CH₂CH═CH₂ 879 CH₃ 4-OCH₂C₆H₄-4-Cl CH₂CH═CHCH₃ 880 CH₃4-OCH₂C₆H₄-4-Cl CH₂CH═C(CH₃)₂ 881 CH₃ 4-OCH₂C₆H₄-4-Cl CH₂CH═CHCl 882 CH₃4-OCH₂C₆H₄-4-Cl CH₂CH═CCl₂ 883 CH₃ 4-OCH₂C₆H₄-4-Cl CH₂C(CH₃)═CH₂ 884 CH₃4-OCH₂C₆H₄-4-Cl CH₂C≡CH 885 CH₃ 4-OCH₂C₆H₄-4-Cl CH₂Si(CH₃)₃ 886 CH₃4-OCH₂C₆H₄-4-Cl CH₂-c.propyl-2,2-Cl₂ 887 CH₃ 4-OCH₂C₆H₄-4-Cl CH₂CN 888CH₃ 4-OCH₂C₆H₄-4-Cl CH₂COOC₂H₅ 889 CH₃ 4-OCH₂C₆H₄-4-Cl CH(CH₃)COOC₂H₅890 CH₃ 4-OCH₂C₆H₄-4-Cl CH₂C₆H₄-3-CF₃ 891 CH₃ 4-OCH₂C₆H₄-4-ClCH₂C₆H₄-4-F 892 CH₃ 4-OCH₂C₆H₄-4-Cl CH₂C₆H₄-3-F 893 CH₃ 4-OCH₂C₆H₄-4-ClCH₂C₆H₄-2-F 894 CH₃ 4-OCH₂C₆H₄-4-Cl C(═O)OC₂H₅ 895 CH₃ 4-OCH₂C₆H₄-4-ClC(═O)NHCH₃ 896 CH₃ 4-OCH₂C₆H₄-4-Cl C(═O)C(═O)OC₂H₅ 797 CH₃4-OCH₂C₆H₃-3,4-Cl₂ CH₃ 898 CH₃ 4-OCH₂C₆H₃-3,4-Cl₂ C₂H₅ 899 CH₃4-OCH₂C₆H₃-3,4-Cl₂ n-C₃H₇ 900 CH₃ 4-OCH₂C₆H₃-3,4-Cl₂ i-C₃H₇ 901 CH₃4-OCH₂C₆H₃-3,4-Cl₂ n-C₄H₉ 902 CH₃ 4-OCH₂C₆H₃-3,4-Cl₂ n-C₆H₁₃ 903 CH₃4-OCH₂C₆H₃-3,4-Cl₂ CH₂F 904 CH₃ 4-OCH₂C₆H₃-3,4-Cl₂ CHF₂ 905 CH₃4-OCH₂C₆H₃-3,4-Cl₂ CH₂CF₃ 906 CH₃ 4-OCH₂C₆H₃-3,4-Cl₂ CH₂CH═CH₂ 907 CH₃4-OCH₂C₆H₃-3,4-Cl₂ CH₂CH═CHCH₃ 908 CH₃ 4-OCH₂C₆H₃-3,4-Cl₂ CH₂CH═C(CH₃)₂909 CH₃ 4-OCH₂C₆H₃-3,4-Cl₂ CH₂CH═CHCl 910 CH₃ 4-OCH₂C₆H₃-3,4-Cl₂CH₂CH═CCl₂ 911 CH₃ 4-OCH₂C₆H₃-3,4-Cl₂ CH₂C(CH₃)═CH₂ 912 CH₃4-OCH₂C₆H₃-3,4-Cl₂ CH₂C≡CH 913 CH₃ 4-OCH₂C₆H₃-3,4-Cl₂ CH₂Si(CH₃)₃ 914CH₃ 4-OCH₂C₆H₃-3,4-Cl₂ CH₂-c.propyl-2,2-Cl₂ 915 CH₃ 4-OCH₂C₆H₃-3,4-Cl₂CH₂CN 916 CH₃ 4-OCH₂C₆H₃-3,4-Cl₂ CH₂COOC₂H₅ 917 CH₃ 4-OCH₂C₆H₃-3,4-Cl₂CH(CH₃)COOC₂H₅ 918 CH₃ 4-OCH₂C₆H₃-3,4-Cl₂ CH₂C₆H₄-3-CF₃ 919 CH₃4-OCH₂C₆H₃-3,4-Cl₂ CH₂C₆H₄-4-F 920 CH₃ 4-OCH₂C₆H₃-3,4-Cl₂ CH₂C₆H₄-3-F921 CH₃ 4-OCH₂C₆H₃-3,4-Cl₂ CH₂C₆H₄-2-F 922 CH₃ 4-OCH₂C₆H₃-3,4-Cl₂C(═O)OC₂H₅ 923 CH₃ 4-OCH₂C₆H₃-3,4-Cl₂ C(═O)NHCH₃ 924 CH₃4-OCH₂C₆H₃-3,4-Cl₂ C(═O)C(═O)OC₂H₅

In Tables 2.1 and 2.2, the ¹³C-NMR data of the compounds1-[4-(3-trifluoromethyl-phenylmethoxy)-phenyl]-1,2-propanedione1-E-[methyloxime]-2-oxime and1-[4-(3-trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione1-Z-[methyloxime]-2-oxime (which was prepared by one of the knownprocesses and from which the E/Z isomer mixture formed in thepreparation was isolated) or, respectively, methyl2-[[[(1-methyl-2-(4-(3-tri-fluoromethylphenylmethoxy)-phenyl)-2-E-[methoxyimino]ethylidene)amino]oxy]methyl]-α-(methoxymethylene)-phenylacetate(compound A225 in Table 1) are shown. The similar chemical shifts ofatoms 1 and 4 of compound A in Table 2.1 and those in Table 2.2 confirmthe E configuration of the compounds of the formula I.

TABLE 2.1 ¹³C-NMR shifts and ¹Jcc coupling constants of 1-[4-(3-trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione1-E-[methyloxime]-2-oxime (A) and1-[4-(3-trifluoromethylphenylmethoxy)-phenyl]-1,2-propanedione1-Z-[methyloxime]-2-oxime (B)

Compound Atom No. Shift δ (ppm) Coupling ¹Jcc (Hz) A 1 125.6 J₁₂ = 56.03 155.0 J₂₃ = 72.0 4 10.1 J₃₄ = 43.0 B 1 127.8 J₁₂ = 69.0 3 152.1 J₂₃ =56.5 4 14.4 J₃₄ = 41.5

TABLE 2.2 ¹³C-NMR shifts of methyl2-[[[(1-methyl-2-(4-(3-trifluoromethylphenylmethoxy)-phenyl)-2-E-[methoxyimino]ethylidene)amino]oxy]methyl]-α-(methoxymethylene)-phenylacetate (compound 1.225)

Atom No. Shift δ (ppm) 1 124.9 2 155.1 3 155.0 4 11.1

What is claimed is:
 1. A process for the preparation of a compound ofthe formula

and, where appropriate, their tautomers, in each case in the free formor salt form, in which either X is CH or N, Y is OR, and Z is O, or X isN, Y is NHR₈ and Z is O, S or S(═O); R₁ is C₁-C₄alkyl; R₂ is H,C₁-C₄alkyl, halogeno-C₁-C₄alkyl, C₃-C₆cycloalkyl or C₁-C₄alkoxymethyl;R₃ and R₄ independently of one another are H, C₁-C₄alkyl, C₁-C₄alkoxy,OH, CN, NO₂, a (C₁-C₄alkyl)₃—Si group, where the alkyl groups can beidentical or different, halogen, (C₁-C₄alkyl)S(═O)_(m),(halogeno-C₁-C₄alkyl)S(═O)_(m), halogeno-C₁-C₄alkyl orhalogeno-C₁-C₄alkoxy; R₅ is C₁-C₆alkyl, halogeno-C₁-C₆alkyl,C₁-C₆alkoxy, halogeno-C₁-C₆alkoxy, C₁-C₆alkylthio,halogen-C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, halogeno-C₁-C₆alkylsulfinyl,C₁-C₆alkylsulfonyl, halogeno-C₁-C₆alkylsulfonyl, C₁-C₆alkoxy-C₁-C₆alkyl,halogeno-C₁-C₆alkoxy-C₁-C₆alkyl, C₁-C₆alkylthio-C₁-C₆alkyl,halogeno-C₁-C₆alkylthio-C₁-C₆alkyl, C₁-C₆alkylsulfinyl-C₁-C₆alkyl,halogeno-C₁-C₆-alkylsulfinyl-C₁-C₆alkyl, C₁-C₆-alkylsulfonyl-C₁-C₆alkyl,halogeno-C₁-C₆-alkylsulfonyl-C₁-C₆alkyl, C₁-C₆-alkylcarbonyl,halogeno-C₁-C₆-alkylcarbonyl, C₁-C₆-alkoxycarbonyl,halogeno-C₁-C₆-alkoxycarbonyl, C₁-C₆-alkylaminocarbonyl,C₁-C₆-alkoxyiminomethyl; di(C₁-C₆alkyl)-aminocarbonyl, where the alkylgroups can be identical or different; C₁-C₆-alkylaminothiocarbonyl;di(C₁-C₆alkyl)aminothiocarbonyl, where the alkyl groups can be identicalor different; C₁-C₆-alkylamino, di(C₁-C₆alkyl)-amino, where the alkylgroups can be identical or different; halogen, NO₂, CN, SF₅, thioamido,thiocyanatomethyl; an unsubstituted or mono- to tetrasubstitutedC₁-C₄alkylenedioxy group, where the substituents are selected from thegroup consisting of C₁-C₄alkyl and halogen; or QR₆, where, if n isgreater than 1, the radicals R₅ can be identical or different; R₆ isC₂-C₆alkenyl or C₂-C₆ alkynyl, which are unsubstituted or substituted by1 to 3 halogen atoms; (C₁-C₄alkyl)₃Si, where the alkyl groups can beidentical or different; CN or an unsubstituted or mono- topentasubstituted C₃-C₆cycloalkyl, aryl or heterocyclyl group, where thesubstituents are selected from the group consisting of halogen,C₁-C₆alkyl, halogeno-C₁-C₆alkyl, C₁-C₆alkoxy, halogeno-C₁-C₆alkoxy,phenoxy, naphthoxy and CN; A is a direct bond, C₁-C₁₀alkylene, —C(═O)—,—C(═S)— or halogeno-C₁-C₁₀alkylene and R₇ is a radical R₁₀, or A isC₁-C₁₀alkylene, —C(═O)—, —C(═S)— or halogeno-C₁-C₁₀alkylene and R₇ isOR₁₀, N(R₁₀)₂, where the radicals R₁₀ can be identical or different, or—S(═O)_(q)R₁₀; R₈ is H or C₁-C₄alkyl; R₉ is methyl, fluoromethyl ordifluoromethyl; R₁₀ is H; an unsubstituted or substituted C₁-C₆alkyl,C₂-C₆alkenyl or C₂-C₆alkynyl group, where the substituents are selectedfrom the group consisting of halogen; (C₁-C₄alkyl)₃Si, where the alkylgroups can be identical or different; C₃-C₆cyclo-alkyl, which isunsubstituted or substituted by halogen; C₁-C₆alkoxycarbonyl, which isunsubstituted or substituted by halogen; unsubstituted or substitutedaryl, where the substituents are selected from the group consisting ofhalogen, halogeno-C₁-C₄alkyl and CN; a (C₁-C₆alkyl)₃Si group, where thealkyl groups can be identical or different; C₃-C₆cycloalkyl, which isunsubstituted or substituted by halogen; C₁-C₆alkoxycarbonyl which isunsubstituted or substituted by halogen; or an unsubstituted orsubstituted aryl or heterocyclyl group, where the substituents areselected from the group consisting of halogen and halogeno-C₁-C₄alkyl; Qis a direct bond, C₁-C₈alkylene, C₂-C₆alkenylene, C₂-C₆alkynylene, O,O(C₁-C₆alkylene), (C₁-C₆alkylene)O, S(═O)_(p), S(═O)_(p)(C₁-C₆alkylene)or (C₁-C₆alkylene)S(═O)_(p); m is 0, 1 or 2; n is 0, 1, 2, 3, 4 or 5; pis 0, 1 or 2; and q is 0, 1 or 2, and the C═N double bond marked with Ehas the E configuration, which comprises a2) reacting a compound of theformula

 in which A, R₂, R₅, R₇ and n are as defined for formula (I) and the C═Ndouble bond marked with E has the E configuration, or a tautomerthereof, in each case in the free form or in the salt form, with acompound of the formula

 in which X, Y, Z, R₃, R₄ and R₉ are as defined for formula (I), or, ifappropriate, a tautomer thereof, in each case in the free form or insalt form, wherein the compound of formula (IV) is obtained by b1)reacting a compound of the formula

 in which R₂, R₅ and n are as defined for formula (I) and the C═N doublebond marked with E has the E configuration, or a tautomer thereof, ineach case in the free form or in salt form, with a compound of theformula R₇—A—X₂  (VII),  in which A and R₇ are as defined for formula(I) and X₂ is a leaving group, wherein the compound of formula (VI) isobtained by c) reacting a compound of the formula

 in which R₂, R₅ and n are as defined for formula (I), or a tautomerthereof, in each case in the free form or in salt form, with aC₁-C₆alkyl nitrite.
 2. A process according to claim 1, wherein one ormore of steps a2), b1), and c) is carried out in the presence of a base.3. A process according to claim 2, wherein the base is selected from thegroup consisting of alkali metal and alkaline earth metal hydroxides,hydrides, amides, alkanolates, acetates, carbonates, dialkylamides andalkylsilylamides.
 4. A process according to claim 3, wherein the base issodium hydroxide.
 5. A process according to claim 1, wherein one or moreof steps a2), b1), and c) is carried out in the presence of a solvent ordiluent or of a mixture thereof.
 6. A process according to claim 5,wherein the solvent is selected from the group consisting of methanol,ethanol, propanol, isopropanol, butanol, ethylene glycol and glycerol.7. A process according to claim 6, wherein the solvent is methanol.
 8. Aprocess according to claim 1, wherein step a2) is carried out in atemperature range from about 10° to about 30°, step b1) is carried outin a temperature range from about 10° to about 60°, and step c) iscarried out in a temperature range from about 0° to about 40°.
 9. Aprocess according to claim 1, wherein the reaction time for step a2) isbetween about 0.5 and about 2 hours, the reaction time for step b1) isbetween about 0.5 and about 5 hours, and the reaction time for step c)is between about 0.5 and about 3 hours.